Benzyl Bromide → 4-Benzyloxy-1-bromo-isoquinoline-3-carboxylic acid butyl ester

HRID 1406222Notes

Reaction equation

HRID 1406222 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:19])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:19])[C:11]2[C:16]([C:17]=1[O:18][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 860145411-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Product 1

HCID 860145034-Benzyloxy-1-bromo-isoquinoline-3-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (6.48 g, 20 mmol; Example D-28 a), benzyl bromide (3.6 ml, 30 mmol), K2CO3 (12.44 g, 90 mmol) and acetone (300 ml) was refluxed with stirring for 2.5 d. The solvent was then evaporated in vacuo. To the residue was added water (100 ml) and the mixture was extracted with EtOAc (100 ml). The organic phase was dried over MgSO4 and evaporated in vacuo to give the title compound as a yellowish solid; MS-(+)-ion: M+1=414.1.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. additionTo the residue was added water (100 ml)
  3. extractionthe mixture was extracted with EtOAc (100 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-abcc905f9e6a4a4eaf28f8b4242b8667
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

Loading…