Pyridine → HCID 22326675, compound
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=O.[N:12]1C=CC=[CH:14][CH:13]=1.C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH3:11][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]2[C:3]=1[CH:4]=[N:12][C:13]([CH3:14])=[N:1]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.