(2,3-dimethylphenyl)methanamine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a dry nitrogen atmosphere, a stirred mixture of 5.56 grams (0.041 mole) of 2,3-dimethylbenzylamine and 5.0 grams (0.041 mole) of 2-chloroethylisothiocyanate in 100 mL of 1,4-dioxane was heated to 80° C. where it stirred for about 18 hours. The reaction mixture was allowed to cool and a solid precipitate that had formed was collected by filtration. The solid was rinsed with diethyl ether and was dried under reduced pressure to yield 8.0 grams of the title compound. The NMR spectrum was consistent with the proposed structure. to cool a solid precipitate that had formed was collected by filtration The solid was rinsed with diethyl ether was dried under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1.0 gram (0.0074 mole) of 2,3-dimethylbenzylamine and 0.69 gram (0.0081 mole) of 2-chloroethylisocyanate in 10 mL of 1,4-dioxane was heated to reflux where it stirred for about 18 hours. The reaction mixture was allowed to cool and an aqueous solution of sodium hydroxide (4.0 mL of a 3.0 molar solution) was added. The reaction mixture was heated to reflux for about 18 hours then allowed to cool to ambient temperature. The reaction mixture was concentrated under reduced pressure to leave a viscous oil residue. The residue was suspended in 50 mL of ethyl acetate and washed with 20 mL of water. The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid. The aqueous extract was made basic by adding 3.0 molar aqueous sodium hydroxide and the basic mixture was extracted with 50 mL of ethyl acetate. The extract was dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield 0.81 gram of the title compound as an oil. The NMR spectrum was consistent with the proposed structure. was heated to reflux where it to cool The reaction mixture was heated to reflux for about 18 hours The reaction mixture was concentrated under reduced pressure to leave a viscous oil residue washed with 20 mL of water The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid The aqueous extract by adding 3.0 molar aqueous sodium hydroxide the basic mixture was extracted with 50 mL of ethyl acetate The extract was dried with sodium sulfate filtered the filtrate concentrated under reduced pressure

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a dry nitrogen atmosphere, a stirred mixture of 5.56 grams (0.041 mole) of 2,3-dimethylbenzylamine and 5.0 grams (0.041 mole) of 2-chloroethylisothiocyanate in 100 mL of 1,4-dioxane was heated to 80° C. where it stirred for about 18 hours. The reaction mixture was allowed to cool and a solid precipitate that had formed was collected by filtration. The solid was rinsed with diethyl ether and was dried under reduced pressure to yield 8.0 grams of the title compound. The NMR spectrum was consistent with the proposed structure. to cool a solid precipitate that had formed was collected by filtration The solid was rinsed with diethyl ether was dried under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1.0 gram (0.0074 mole) of 2,3-dimethylbenzylamine and 0.69 gram (0.0081 mole) of 2-chloroethylisocyanate in 10 mL of 1,4-dioxane was heated to reflux where it stirred for about 18 hours. The reaction mixture was allowed to cool and an aqueous solution of sodium hydroxide (4.0 mL of a 3.0 molar solution) was added. The reaction mixture was heated to reflux for about 18 hours then allowed to cool to ambient temperature. The reaction mixture was concentrated under reduced pressure to leave a viscous oil residue. The residue was suspended in 50 mL of ethyl acetate and washed with 20 mL of water. The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid. The aqueous extract was made basic by adding 3.0 molar aqueous sodium hydroxide and the basic mixture was extracted with 50 mL of ethyl acetate. The extract was dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield 0.81 gram of the title compound as an oil. The NMR spectrum was consistent with the proposed structure. was heated to reflux where it to cool The reaction mixture was heated to reflux for about 18 hours The reaction mixture was concentrated under reduced pressure to leave a viscous oil residue washed with 20 mL of water The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid The aqueous extract by adding 3.0 molar aqueous sodium hydroxide the basic mixture was extracted with 50 mL of ethyl acetate The extract was dried with sodium sulfate filtered the filtrate concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 2,3-dimethyl-benzylamine (87 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (140 mg, 1.45 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-(2,3-dimethyl-benzylamino)-2H-phthalazin-1-one: 43 mg (23.6%): m/z (M+H)=314. 1H-NMR (DMSO-d6) δ: 12.34 (s, 1H), 7.92 (d, 1H), 7.44 (m, 1H), 7.10 (m, 4H), 6.85 (s, 1H), 4.36 (d, 2H), 2.62 (s, 3H), 2.22 (s, 3H). to cool washed with water (25 mL) The organic layer was dried over anhydrous sodium sulfate concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), 2,3-dimethyl-benzylamine (87 mg, 0.64 mmol), Pd2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (140 mg, 1.45 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-(2,3-dimethyl-benzylamino)-2H-phthalazin-1-one: 43 mg (23.6%): m/z (M+H)=314. 1H-NMR (DMSO-d6) δ: 12.34 (s, 1H), 7.92 (d, 1H), 7.44 (m, 1H), 7.10 (m, 4H), 6.85 (s, 1H), 4.36 (d, 2H), 2.62 (s, 3H), 2.22 (s, 3H). to cool washed with water (25 mL) The organic layer was dried over anhydrous sodium sulfate concentrated

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Under a dry nitrogen atmosphere, a stirred mixture of 5.56 grams (0.041 mole) of 2,3-dimethylbenzylamine and 5.0 grams (0.041 mole) of 2-chloroethylisothiocyanate in 100 mL of 1,4-dioxane was heated to 80° C. where it stirred for about 18 hours. The reaction mixture was allowed to cool and a solid precipitate that had formed was collected by filtration. The solid was rinsed with diethyl ether and was dried under reduced pressure to yield 8.0 grams of the title compound. The NMR spectrum was consistent with the proposed structure. to cool a solid precipitate that had formed was collected by filtration The solid was rinsed with diethyl ether was dried under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1.0 gram (0.0074 mole) of 2,3-dimethylbenzylamine and 0.69 gram (0.0081 mole) of 2-chloroethylisocyanate in 10 mL of 1,4-dioxane was heated to reflux where it stirred for about 18 hours. The reaction mixture was allowed to cool and an aqueous solution of sodium hydroxide (4.0 mL of a 3.0 molar solution) was added. The reaction mixture was heated to reflux for about 18 hours then allowed to cool to ambient temperature. The reaction mixture was concentrated under reduced pressure to leave a viscous oil residue. The residue was suspended in 50 mL of ethyl acetate and washed with 20 mL of water. The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid. The aqueous extract was made basic by adding 3.0 molar aqueous sodium hydroxide and the basic mixture was extracted with 50 mL of ethyl acetate. The extract was dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield 0.81 gram of the title compound as an oil. The NMR spectrum was consistent with the proposed structure. was heated to reflux where it to cool The reaction mixture was heated to reflux for about 18 hours The reaction mixture was concentrated under reduced pressure to leave a viscous oil residue washed with 20 mL of water The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid The aqueous extract by adding 3.0 molar aqueous sodium hydroxide the basic mixture was extracted with 50 mL of ethyl acetate The extract was dried with sodium sulfate filtered the filtrate concentrated under reduced pressure