Methanol → Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate
Reaction equation
[C:1](O)(=O)[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[C:14](CC1C=CC=CC=1C=O)(O)=[O:15].[OH-:26].[K+].[CH3:28][OH:29]>>[O:26]=[C:4]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:1]=[C:2]([C:28]([O:15][CH3:14])=[O:29])[NH:3]1Participants
4
Conditions
- Temperature
- 65 °C
Procedure
The 2-carboxymethylbenzaldehyde hippuric acid adduct from above (1.0 g, 3.3 mmoles) was dissolved in methanol (20 mls) and solid potassium hydroxide (0.37 g, 6.6 mmoles) was added. The clear solution was heated (65° C.) for 1 hour. The reaction was evaporated and the solid residue partitioned between water (25 mls) and ethyl acetate (25 mls). The aqueous layer was further extracted with ethyl acetate (2×10 mls) and the combined ethyl acetate extracts washed with brine (10 mls) water (10 mls). After drying over magnesium sulphate the solution was evaporated to leave a yellow solid (0.68 g, 99% yield).