Hydrochloric Acid → 5-(Benzyloxy)-1,4-dihydro-4-oxo-2-pyridinecarboxylic acid, ethyl ester
Reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:20](O)[CH3:21]>>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([C:15]([O:17][CH2:20][CH3:21])=[O:16])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A suspension of 5-(benzyloxy)-1,4-dihydro-4-oxo-2-pyridinecarboxylic acid (8.24 g, 33.6 mmole) in 120 ml of ethanol was cooled to 0° C. and treated with a stream of dry HCl for 15 minutes. The resulting mixture was heated at 50° C. for 5.5 hours. The volatiles were removed in vacuo and the residue was treated with water. While cooling, the pH was raised to 7 with saturated potassium bicarbonate and the resulting mixture was extracted with dichloromethane. The extracts were washed with brine and dried over sodium sulfate. Filtration and concentration in vacuo produced 7.32 g of the title compound.