Hydrochloric Acid → 7-Methoxy-isoquinoline-N-oxide hydrochloride

HRID 2304295Notes

Reaction equation

HRID 2304295 reaction equation
[Cl:1]C1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][N:20]=[CH:21]2)=[CH:16][CH:15]=1.CO.Cl>ClCCl.C(OCC)C>[ClH:1].[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][N+:20]([O-:6])=[CH:21]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 70297m-Chloroperbenzoic acidHCID 5943757-Methoxyisoquinoline

Product 1

HCID 226656837-Methoxy-isoquinoline-N-oxide hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

At room temperature 58 g of m-chloroperoxybenzoic acid (purity 75%) were added in portions to a stirred solution of 7-methoxy-isoquinoline (35.9 g) in 500 mL of dichloromethane. Stirring was continued for 3 hours and subsequently methanol (400 mL) was added. The bulk was reduced to 300 mL and 325 mL of a saturated solution of hydrogen chloride in diethyl ether were added. Dilution with 600 mL of diethyl ether afforded precipitation of yellow crystals, which were separated by filtration, washed with chilled diethyl ether and dried in vacuo. Yield: 41.3 g (87%); m.p. 185-187° C.; (+)-FAB-MS: 176 (MH+-HCl).

Workup

  1. additionwere added
  2. customprecipitation of yellow crystals, which
  3. customwere separated by filtration
  4. washwashed with chilled diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f308ad24ba88412fb0a54642d20b8490
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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