Ammonia → 6-Hydroxy-7-methylisoquinolin-1(2H)-one

HRID 1436003Notes

Reaction equation

HRID 1436003 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[C:13](=[O:18])[NH:12][CH:11]=[CH:10]2.N>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[CH3:17])[C:13](=[O:18])[NH:12][CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 181763916-Methoxy-7-methylisoquinolin-1(2H)-one

Product 1

HCID 688755126-Hydroxy-7-methylisoquinolin-1(2H)-oneYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1 M solution of boron tribromide (2.9 ml, 2.91 mmol) was added dropwise to a stirred suspension of 6-methoxy-7-methyl-2H-isoquinolin-1-one (100 mg, 0.53 mmol) in 1 ml of dichloromethane at 0-4° C. (ice bath). After stirring for 1 day at ambient temperature the reaction mixture was poured into ice and the pH was adjusted to 9 by adding concentrated aqueous ammonia. The precipitated material was collected by filtration, washed with water, and dried in vacuo to give 6-Hydroxy-7-methyl-2H-isoquinolin-1-one (51 mg, 55%), El-MS: 176.6 [M+H]+

Workup

  1. additionwas poured into ice
  2. filtrationThe precipitated material was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9790c304bd6e42f5bec7648f72f23605
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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