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C1=CC=C2C=C(C(=CC2=C1)CO)N製品情報
(3-aminonaphthalen-2-yl)methanol (CAS 141281-58-5) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
想定用途
専門的研究・工業用途限定
データベース ID 10374898
安全上の注意
For professional research and industrial use only. Review the supplier safety data sheet before handling.
合成データ
11 反応 · 11 文献
反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-64767bc95ce54764aebe4befd001a769反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-19a9363eb072442abe68381f4e4139d7反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A solution of (3-amino-2-naphthyl)methanol (500 mg, 2.89 mmol) in water (3 mL), acetone (3 mL) and concentrated HCl (1.6 mL) was cooled to 0° C. and a solution of sodium nitrite (219 mg, 3.18 mmol) in water (0.7 mL) was added. The reaction was stirred for 2 h at 0° C. and a solution of potassium iodide (719 mg, 4.33 mmol) and concentrated H2SO4 (0.16 mL) in water (1.2 mL) was added. The reaction mixture was heated at 60° C. for 2-3 h. The reaction mixture was cooled to room temperature and 50% saturated Na2SO3 (30 mL) was added. The mixture was extracted with CH2Cl2 (3×20 mL) and the combined extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 25×160 mm, 0-40% EtOAc in hexanes gradient) to afford (3-iodo-2-naphthyl)methanol. Rf=0.47 (20% EtOAc/hexanes). 1H NMR (600 MHz, CD3OD): δ 8.35 (s, 1H); 7.91 (s, 1H); 7.81 (d, J=8.0 Hz, 1H); 7.71 (d, J=8.0 Hz, 1H); 7.47-7.42 (m, 2H); 4.69 (s, 2H). The reaction mixture was heated at 60° C. for 2-3 h The reaction mixture was cooled to room temperature The mixture was extracted with CH2Cl2 (3×20 mL) the combined extracts were washed with brine (20 mL) dried (Na2SO4) concentrated in vacuo to give the crude product This was purified by flash chromatography (Si, 25×160 mm, 0-40% EtOAc in hexanes gradient)
ソース ID: ord-f5f7cc78c6124da8a1151e8529a66a3d反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A solution of 3-amino-2-naphthoic acid (85%, 1.17 g, 5.34 mmol) in dry THF (20 mL) was added dropwise over 30 min to a stirred solution of lithium aluminum hydride (95%, 0.53 g, 13.4 mmol) in dry THF (20 mL) at 0° C. under N2. The mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was adjusted to basic pH with 1N NaOH (20 mL). The mixture was filtered and extracted with Et2O (4×100 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-amino-2-naphthyl)methanol. LCMS calc.=174.1; found=174.2 (M+1)+. 1H NMR (500 MHz, CD3OD): δ 7.66 (d, J=8.0 Hz, 1H); 7.61 (s, 1H); 7.55 (d, J=8.2 Hz, 1H); 7.30-7.27 (m, 1H); 7.18-7.14 (m, 1H); 7.08 (s, 1H); 4.74 (s, 2H). The mixture was filtered extracted with Et2O (4×100 mL) The combined extracts were dried (MgSO4) concentrated in vacuo
ソース ID: ord-348fc64e6adf44ebbb9a5667e018867c反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A solution of 3-amino-2-naphthoic acid (85%, 1.17 g, 5.34 mmol) in dry THF (20 mL) was added dropwise over 30 min to a stirred solution of lithium aluminum hydride (95%, 0.53 g, 13.4 mmol) in dry THF (20 mL) at 0° C. under N2. The mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was adjusted to basic pH with 1N NaOH (20 mL). The mixture was filtered and extracted with Et2O (4×100 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-amino-2-naphthyl)methanol. LCMS calc.=174.1; found=174.2 (M+1)+. 1H NMR (500 MHz, CD3OD): δ 7.66 (d, J=8.0 Hz, 1H); 7.61 (s, 1H); 7.55 (d, J=8.2 Hz, 1H); 7.30-7.27 (m, 1H); 7.18-7.14 (m, 1H); 7.08 (s, 1H); 4.74 (s, 2H). The mixture was filtered extracted with Et2O (4×100 mL) The combined extracts were dried (MgSO4) concentrated in vacuo
ソース ID: ord-348fc64e6adf44ebbb9a5667e018867c反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A solution of 3-amino-2-naphthoic acid (85%, 1.17 g, 5.34 mmol) in dry THF (20 mL) was added dropwise over 30 min to a stirred solution of LiAlH4 (95%, 0.53 g, 13.4 mmol) in dry THF (20 mL) at 0° C. under N2. The mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was adjusted to basic pH with 1N NaOH (20 mL). The mixture was filtered and extracted with Et2O (4×100 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-amino-2-naphthyl)methanol (0.88 g, 95%). LCMS calc.=174.1; found=174.2 (M+1)+. 1H NMR (500 MHz, CD3OD): δ 7.66 (d, J=8.0 Hz, 1H); 7.61 (s, 1H); 7.55 (d, J=8.2 Hz, 1H); 7.30-7.27 (m, 1H); 7.18-7.14 (m, 1H); 7.08 (s, 1H); 4.74 (s, 2H). The mixture was filtered extracted with Et2O (4×100 mL) The combined extracts were dried (MgSO4) concentrated in vacuo
ソース ID: ord-573375b169314408a3157da42511d2be反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-19a9363eb072442abe68381f4e4139d7反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: To a solution of 3-amino-2-naphthoic acid (2 g, 10.7 mmol) in THF (11 mL) at 0° C. is added a 1 M solution of borane-tetrahydrofuran complex (27 mL) dropwise over 15 min. The mixture is allowed to warm to ambient temperature and stirred for 6 h. The excess borane-tetrahydrofuran complex is quenched by adding methanol at 0° C., and the solvent evaporated to obtain a yellow solid. The solid is washed with water, EtOAc and then dried under high vacuum to give (3-aminonaphthalen-2-yl)-methanol. The excess borane-tetrahydrofuran complex is quenched by adding methanol at 0° C. the solvent evaporated to obtain a yellow solid The solid is washed with water, EtOAc dried under high vacuum
ソース ID: ord-22a0acca59f44533955a3995f360cc13反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A solution of (3-amino-2-naphthyl)methanol (500 mg, 2.89 mmol) in water (3 mL), acetone (3 mL) and concentrated HCl (1.6 mL) was cooled to 0° C. and a solution of sodium nitrite (219 mg, 3.18 mmol) in water (0.7 mL) was added. The reaction was stirred for 2 h at 0° C. and a solution of potassium iodide (719 mg, 4.33 mmol) and concentrated H2SO4 (0.16 mL) in water (1.2 mL) was added. The reaction mixture was heated at 60° C. for 2-3 h. The reaction mixture was cooled to room temperature and 50% saturated Na2SO3 (30 mL) was added. The mixture was extracted with CH2Cl2 (3×20 mL) and the combined extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 25×160 mm, 0-40% EtOAc in hexanes gradient) to afford (3-iodo-2-naphthyl)methanol. Rf=0.47 (20% EtOAc/hexanes). 1H NMR (600 MHz, CD3OD): δ 8.35 (s, 1H); 7.91 (s, 1H); 7.81 (d, J=8.0 Hz, 1H); 7.71 (d, J=8.0 Hz, 1H); 7.47-7.42 (m, 2H); 4.69 (s, 2H). The reaction mixture was heated at 60° C. for 2-3 h The reaction mixture was cooled to room temperature The mixture was extracted with CH2Cl2 (3×20 mL) the combined extracts were washed with brine (20 mL) dried (Na2SO4) concentrated in vacuo to give the crude product This was purified by flash chromatography (Si, 25×160 mm, 0-40% EtOAc in hexanes gradient)
ソース ID: ord-f5f7cc78c6124da8a1151e8529a66a3d反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A solution of 3-amino-2-naphthoic acid (85%, 1.17 g, 5.34 mmol) in dry THF (20 mL) was added dropwise over 30 min to a stirred solution of lithium aluminum hydride (95%, 0.53 g, 13.4 mmol) in dry THF (20 mL) at 0° C. under N2. The mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was adjusted to basic pH with 1N NaOH (20 mL). The mixture was filtered and extracted with Et2O (4×100 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-amino-2-naphthyl)methanol. LCMS calc.=174.1; found=174.2 (M+1)+. 1H NMR (500 MHz, CD3OD): δ 7.66 (d, J=8.0 Hz, 1H); 7.61 (s, 1H); 7.55 (d, J=8.2 Hz, 1H); 7.30-7.27 (m, 1H); 7.18-7.14 (m, 1H); 7.08 (s, 1H); 4.74 (s, 2H). The mixture was filtered extracted with Et2O (4×100 mL) The combined extracts were dried (MgSO4) concentrated in vacuo
ソース ID: ord-348fc64e6adf44ebbb9a5667e018867c反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: A solution of 3-amino-2-naphthoic acid (85%, 1.17 g, 5.34 mmol) in dry THF (20 mL) was added dropwise over 30 min to a stirred solution of LiAlH4 (95%, 0.53 g, 13.4 mmol) in dry THF (20 mL) at 0° C. under N2. The mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was adjusted to basic pH with 1N NaOH (20 mL). The mixture was filtered and extracted with Et2O (4×100 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-amino-2-naphthyl)methanol (0.88 g, 95%). LCMS calc.=174.1; found=174.2 (M+1)+. 1H NMR (500 MHz, CD3OD): δ 7.66 (d, J=8.0 Hz, 1H); 7.61 (s, 1H); 7.55 (d, J=8.2 Hz, 1H); 7.30-7.27 (m, 1H); 7.18-7.14 (m, 1H); 7.08 (s, 1H); 4.74 (s, 2H). The mixture was filtered extracted with Et2O (4×100 mL) The combined extracts were dried (MgSO4) concentrated in vacuo
ソース ID: ord-573375b169314408a3157da42511d2bePubChem References
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