Water → 6-hydroxyisoquinolin-1(2H)-one

HRID 68990Notes

Reaction equation

HRID 68990 reaction equation
B(Br)(Br)Br.ClCCl.ClCCl.C[O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[NH:18][CH:17]=[CH:16]2.O>ClCCl.CO.CO>[OH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[NH:18][CH:17]=[CH:16]2

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 218898546-methoxyisoquinolin-1(2H)-oneHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 105111706-hydroxyisoquinolin-1(2H)-oneYield 43.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A 1.0M boron tribromide/dichloromethane solution (8.5 ml) was added at 0° C. to a dichloromethane solution (50 ml) of 6-methoxy-2H-isoquinolin-1-one (1.0 g). The mixture was stirred at room temperature overnight. Water and methanol were added to the reaction mixture and extraction was carried out with a dichloromethane/methanol mixed solvent (dichloromethane:methanol=10:1). The organic layer was dried with anhydrous sodium sulfate, followed by condensation to dryness under reduced pressure, thereby obtaining the title compound (0.4 g) as a pale yellow solid.

Workup

  1. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  2. customfollowed by condensation to dryness under reduced pressure

Sources & evidence

ORD record
ord-8830016bee6f4688b26af90a31900d8f
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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