6-Methoxy-isoquinoline 2-oxide hydrochloride → 1-Chloro-6-methoxyisoquinoline

HRID 1070556

Reaction equation

HRID 1070556 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[N+:9]([O-])[CH:8]=[CH:7]2>P(Cl)(Cl)(Cl)=O>[Cl:1][C:10]1[C:11]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1

Participants

3

Reactant 1

HCID 223973326-Methoxy-isoquinoline 2-oxide hydrochloride

Product 1

HCID 219010741-Chloro-6-methoxyisoquinoline

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
90 °C

Procedure

6-Methoxy-isoquinoline-N-oxide hydrochloride (1a, 85 g; 400 mmol) was carefully added in portions to phosphoryl chloride (550 mL) at a temperature of 90° C., after which the mixture was stirred for 6 h at 90° C. Excess of phosphoryl chloride was removed in vacuo. The remaining white solid was washed with water, filtered and dried in vacua. Yield: 68 g (88%); white solid; m.p. 72-74° C.; El-MS: 193 (M+).

Workup

  1. customExcess of phosphoryl chloride was removed in vacuo
  2. washThe remaining white solid was washed with water
  3. filtrationfiltered
  4. customdried in vacua

Sources & evidence

ORD record
ord-f65656e336f847d098a261866c2b097a
Source dataset
uspto-grants-2005_06
Patent number
US06903107B1

Linked notes

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