Potassium Hydroxide → 4-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carboxylic acid

HRID 2060409Notes

Reaction equation

HRID 2060409 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]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 667127584-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carboxylic acid benzyl ester

Product 1

HCID 667128304-Benzyloxy-1-methoxymethyl-7-phenoxy-isoquinoline-3-carboxylic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. customwas evaporated in vacuo
  2. additionTo the residue was added water (10 ml)
  3. additionthe mixture was acidified by the addition of aqueous 6N HCl
  4. extractionextracted with EtOAc (2×25 ml)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-898ee1669d5946a9b58d13469da85495
Source dataset
uspto-grants-2012_10
Patent number
US08278325B2

Reaction notes

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