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

HRID 908827Notes

Reaction equation

HRID 908827 reaction equation
C([O:8][C:9]([C:11]1[N:12]=[C:13]([CH2:29][O:30][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]([CH2:29][O:30][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 667131694-Benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acid benzyl ester

Product 1

HCID 667128924-Benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acidYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-Benzyloxy-1-methoxymethyl-isoquinoline-3-carboxylic acid benzyl ester (198 mg, 0.48 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 (25 ml). The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow oil (140 mg); MS-(+)-ion: M+1=324.1.

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 (25 ml)
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34995b5f9dce41d3833ffe0d4044cbcc
Source dataset
uspto-grants-2011_09
Patent number
US08017625B2

Reaction notes

Loading…