Phosphorus oxychloride → 1-Chloro-6-methoxy-3-methylisoquinoline

HRID 1821605Notes

Reaction equation

HRID 1821605 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[NH:8][C:7]([CH3:14])=[CH:6]2.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[C:7]([CH3:14])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 123270606-Methoxy-3-methylisoquinolin-1(2H)-one

Product 1

HCID 578930951-Chloro-6-methoxy-3-methylisoquinoline

Procedure

Isoquinoline-1-one 43 was dissolved in POCl3 (2.5 mL) and heated at reflux for 1h. The excess POCl3 was removed in vacuo and the residue was dissolved in CHCl3. The resulting solution was washed with 1N aq. NaOH, water and saturated ag. NaCl. Evaporation of the solvent gave crude 44 which was used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1h
  3. customThe excess POCl3 was removed in vacuo
  4. dissolutionthe residue was dissolved in CHCl3
  5. washThe resulting solution was washed with 1N aq. NaOH, water and saturated ag
  6. customEvaporation of the solvent
  7. customgave crude 44 which

Sources & evidence

ORD record
ord-691bfe019da5468c974cab34905ed9b7
Source dataset
uspto-grants-2009_10
Patent number
US07608592B2

Reaction notes

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