2-amino-6-methoxybenzaldehyde

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

実験手順: To a stirred solution of 2-amino-6-methoxybenzaldehyde [K. Tsuda et al., Chem. Pharm. Bull. 1962, 10, 856] (1.3 g, 8.6 mmol), pyridine (0.81 g, 10.3 mmol) and toluene (60 mL) was added acetic anhydride (0.97 g, 9.5 mmol). The resulting mixture was heated at reflux for 18 h, cooled, then partitioned between saturated aqueous NaHCO3 (100 mL) and ether (50 mL). The organic phase was dried (Na2SO4) and evaporated in vacuo to give a solid which was purified by chromatography on silica with 0-50% ether in hexane gradient elution to give a colourless solid (1.28 g). The latter was dissolved in 2 M methanolic ammonia (100 mL) and the solution heated at reflux for 3 h, cooled, then evaporated in vacuo. Chromatography of the residue on silica with 0-100% ether in dichloromethane gradient elution gave the title compound (0.92 g, 62%) as a colourless solid. The resulting mixture was heated at reflux for 18 h cooled partitioned between saturated aqueous NaHCO3 (100 mL) and ether (50 mL) The organic phase was dried (Na2SO4) evaporated in vacuo to give a solid which was purified by chromatography on silica with 0-50% ether in hexane gradient elution

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2-Amino-6-methoxy-benzaldehyde (6.00 g, 0.04 mol) and triethylamine (4.4 g, 0.044 mol) is dissolved in THF (20 mL) and cooled to 0° C., then CCl3COCl (7.95 g, 0.044 mol) is added and stirred at 25° C. for 24 h. The mixture is extracted from water with ethylacetate to give the desired product. The mixture is extracted from water with ethylacetate

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of (2-Amino-6-methoxy-phenyl)-methanol (5.00 g, 0.033 mol) and manganese dioxide (13.7 g) in DCM (500 mL) iswas stirred at 25° C. for 24 h. The resulting solid is filtered off, washed with DCM to give the desired product. The resulting solid is filtered off washed with DCM

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

実験手順: To a stirred solution of 2-amino-6-methoxybenzaldehyde [K. Tsuda et al., Chem. Pharm. Bull. 1962, 10, 856] (1.3 g, 8.6 mmol), pyridine (0.81 g, 10.3 mmol) and toluene (60 mL) was added acetic anhydride (0.97 g, 9.5 mmol). The resulting mixture was heated at reflux for 18 h, cooled, then partitioned between saturated aqueous NaHCO3 (100 mL) and ether (50 mL). The organic phase was dried (Na2SO4) and evaporated in vacuo to give a solid which was purified by chromatography on silica with 0-50% ether in hexane gradient elution to give a colourless solid (1.28 g). The latter was dissolved in 2 M methanolic ammonia (100 mL) and the solution heated at reflux for 3 h, cooled, then evaporated in vacuo. Chromatography of the residue on silica with 0-100% ether in dichloromethane gradient elution gave the title compound (0.92 g, 62%) as a colourless solid. The resulting mixture was heated at reflux for 18 h cooled partitioned between saturated aqueous NaHCO3 (100 mL) and ether (50 mL) The organic phase was dried (Na2SO4) evaporated in vacuo to give a solid which was purified by chromatography on silica with 0-50% ether in hexane gradient elution