Potassium Hydroxide → 4-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carboxylic acid
Reaction equation
C([O:8][C:9]([C:11]1[N:12]=[C:13]([CH2:36][O:37][CH3:38])[C:14]2[C:19]([C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:18][CH:17]=[C:16]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:15]=2)=[O:10])C1C=CC=CC=1.[OH-].[K+]>CCO>[CH2:22]([O:21][C:20]1[C:19]2[C:14](=[CH:15][C:16]([O:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:17][CH:18]=2)[C:13]([CH2:36][O:37][CH3:38])=[N:12][C:11]=1[C:9]([OH:10])=[O:8])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
4
Procedure
A mixture of 4-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carboxylic acid benzyl ester (480 mg, 0.95 mmol), KOH (325 mg, 5 mmol) and EtOH (10 ml) was stirred at ambient temperature for 48 h before the solvent was evaporated in vacuo. To the residue was added water (10 ml), the mixture was acidified by the addition of aqueous 6N HCl and extracted with EtOAc (2×25 ml). The combined organic phases were dried over MgSO4 and concentrated in vacuo to give the title compound as a tan solid (355 mg); MS-(−)-ion: M−1=414.1.