Methanol → 5-bromo-6-methoxyisoquinoline-N-oxide hydrochloride

HRID 1436011Notes

Reaction equation

HRID 1436011 reaction equation
[Cl:1]C1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]=[CH:18]2.CO>ClCCl>[ClH:1].[Br:12][C:13]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N+:17]([O-:9])=[CH:18]2

Participants

5

Reactant 3

HCID 887MethanolHCID 70297m-Chloroperbenzoic acidHCID 222265455-Bromo-6-methoxy-isoquinoline

Product 1

HCID 688780245-bromo-6-methoxyisoquinoline-N-oxide hydrochlorideYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperbenzoic acid (1.4 g, 75%) was added in portions to a stirred solution of 5-bromo-6-methoxyisoquinoline (12 g, 5.04 mmol) in dichloromethane (12 ml). The mixture was stirred for 1 h then further dichloromethane (10 ml) added and the mixture stirred for an additional 2 h. Methanol (12 ml) was added and the mixture concentrated in vacuo to ˜9 ml, then 1M hydrochloric acid in diethyl ether (10 ml) was added. The mixture was diluted with ether and filtered, the precipitated solid was washed with diethyl ether and dried in vacuo to give crude 5-bromo-6-methoxyisoquinoline-N-oxide hydrochloride (1.22 g).

Workup

  1. stirringthe mixture stirred for an additional 2 h
  2. concentrationthe mixture concentrated in vacuo to ˜9 ml
  3. addition1M hydrochloric acid in diethyl ether (10 ml) was added
  4. additionThe mixture was diluted with ether
  5. filtrationfiltered
  6. washthe precipitated solid was washed with diethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a3cddaab01a94e84accae8268c62de9f
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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