pentyl nitrite

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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: Acetic anhydride (1.68 mL, 17.8 mmol) was added to a suspension of 3-amino-2-methylbenzyl alcohol (0.82 g, 5.98 mmol) in chloroform (25 mL). Potassium acetate was added and the resulting mixture was stirred at room temperature for 3 h, under reflux for 2 h, and then at room temperature overnight. Amyl nitrite (1.82 mL, 13.7 mmol) and 18-crown-6 (79 mg, 0.3 mmol) were added and the pale yellow cloudy mixture was heated at reflux overnight, then allowed to cool to room temperature and stir for 5 h. The reaction mixture was poured into acetic anhydride (5 mL) and stirred at room temperature overnight. Dichloromethane (20 mL) was added and the solution was washed with sodium hydrogen carbonate solution, water, and brine (10 mL each), dried (Na2SO4), filtered, concentrated, and chromatographed (10-40% ethyl acetate/petroleum ether) to give 1-acetyl-1H-indazole-4-methanol, acetate ester (1.19 g, 86%) as a pale yellow solid. under reflux for 2 h at room temperature overnight the pale yellow cloudy mixture was heated at reflux overnight to cool to room temperature stir for 5 h stirred at room temperature overnight the solution was washed with sodium hydrogen carbonate solution, water, and brine (10 mL each) dried (Na2SO4) filtered concentrated chromatographed (10-40% ethyl acetate/petroleum ether)

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

実験手順: 5-Fluorotoluidine (Example1,B), pyridine and pentyl nitrite are warmed until a vigorous reaction with evolution of gas sets in. This is allowed to proceed without heating until it has subsided (20 minutes) and the mixture is boiled under reflux for another 100 minutes. The excess pyridine is removed under reduced pressure to yield the title product. without heating until it (20 minutes) under reflux for another 100 minutes The excess pyridine is removed under reduced pressure

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

実験手順: Concentrated hydrochloric acid (7.8 ml) was added dropwise over 1.5 hour to a mixture of 1-(p-methyl)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.CH3, R1 =R2 =CH3) (12.85 g) and amyl nitrite (11.7 ml) in glacial acetic acid (15.6 ml) at -5° to 0° (ice-salt bath). After a further 1 hour at -5° to 0°, the mixture was filtered. The yellow solid so obtained was washed with acetone and recrystallised from acetone to give the nitrosochloride (V) (7.5 g, yield 42%) as white crystals, m.p. 144°-5° (decomp.). the mixture was filtered The yellow solid so obtained was washed with acetone recrystallised from acetone

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

実験手順: Concentrated hydrochloric acid (7.8 ml) was added dropwise over 1.5 hour to a mixture of 1-(p-methyl)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.CH3, R1 =R2 =CH3) (12.85 g) and amyl nitrite (11.7 ml) in glacial acetic acid (15.6 ml) at -5° to 0° (ice-salt bath). After a further 1 hour at -5° to 0°, the mixture was filtered. The yellow solid so obtained was washed with acetone and recrystallised from acetone to give the nitrosochloride (V) (7.5 g, yield 42%) as white crystals, m.p. 144°-5° (decomp.). the mixture was filtered The yellow solid so obtained was washed with acetone recrystallised from acetone

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

実験手順: Concentrated hydrochloric acid (28.4 ml) was added dropwise over 1 hour to a mixture of 1-(p-chloro)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.Cl, R1 =R2 =CH3) (56.1 g) and amyl nitrite (42.6 ml) in glacial acetic acid (56.7 ml) at -5° to 0° (ice-salt bath). After a further 1 hour at -5° to 0°, the mixture was filtered. The solid so obtained was washed with benzene and recrystallised from benzene after drying to give the nitrosochloride (V) (35.31 g, yield 47%) as pale yellow crystals, m.p. 124°-5° (decomp.). the mixture was filtered The solid so obtained was washed with benzene recrystallised from benzene after drying

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

実験手順: Concentrated hydrochloric acid (28.4 ml) was added dropwise over 1 hour to a mixture of 1-(p-chloro)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.Cl, R1 =R2 =CH3) (56.1 g) and amyl nitrite (42.6 ml) in glacial acetic acid (56.7 ml) at -5° to 0° (ice-salt bath). After a further 1 hour at -5° to 0°, the mixture was filtered. The solid so obtained was washed with benzene and recrystallised from benzene after drying to give the nitrosochloride (V) (35.31 g, yield 47%) as pale yellow crystals, m.p. 124°-5° (decomp.). the mixture was filtered The solid so obtained was washed with benzene recrystallised from benzene after drying

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

実験手順: Concentrated hydrochloric acid (7.8 ml) was added dropwise over 1 hour to a mixture of 1-(p-methoxy)phenoxy-3-methylbut-2-ene (VI; R=CH2OC6H4.OCH3, R1 =R2 =CH3) (12.0 g) and amyl nitrite (11.7 ml) in glacial acetic acid (15.6 ml) at 0° C. (ice-salt bath). A white precipitate separated and this was filtered off and dried to give the nitrosochloride (V) (8.0 g, yield 50%) as colourless crystals, m.p. 137°. A white precipitate separated this was filtered off dried