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

HRID 1618160Notes

Reaction equation

HRID 1618160 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-7fc29f516baf4154acb18c4a905581a8
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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