Potassium Hydroxide → 4-Benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carboxylic acid

HRID 523797Notes

Reaction equation

HRID 523797 reaction equation
C([O:8][C:9]([C:11]1[N:12]=[C:13]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[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]=[CH:16][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][CH:16]=[CH:17][CH:18]=2)[C:13]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])=[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 667128144-Benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carboxylic acid benzyl ester

Product 1

HCID 667131084-Benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carboxylic acidYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-benzyloxy-1-dimethylcarbamoyl-isoquinoline-3-carboxylic acid benzyl ester (308 mg, 0.7 mmol), KOH (325 mg, 5 mmol) and EtOH (10 ml) was stirred at ambient temperature for 18 h before the solvent was evaporated in vacuo. To the residue was added water (25 ml) and the mixture was washed with Et2O (2×25 ml). Then the solution was acidified by 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 yellowish gum (220 mg); MS-(+)-ion: M+1=351.0.

Workup

  1. customwas evaporated in vacuo
  2. additionTo the residue was added water (25 ml)
  3. washthe mixture was washed with Et2O (2×25 ml)
  4. additionThen the solution was acidified by addition of aqueous 6N HCl
  5. extractionextracted with EtOAc (2×25 ml)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8fef88c96534cc7b391292ba8ae6c66
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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