Phosphorus oxychloride → 1-Chloro-4-phenyl-isoquinoline-3-carboxylic acid ethyl ester

HRID 2060514Notes

Reaction equation

HRID 2060514 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](O)[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:25]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Cl:25])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470308HCID 178470308, compound

Product 1

HCID 860146021-Chloro-4-phenyl-isoquinoline-3-carboxylic acid ethyl ester

Procedure

A mixture of 1-hydroxy-4-phenyl-isoquinoline-3-carboxylic acid ethyl ester (1.17 g, 4 mmol; can be obtained according to A. Marsili et al., Ann. Chim. (Rome), 1962, 52, 112-120), and concentrated POCl3 (10 ml) was refluxed with stirring for 1 h. Then the mixture was concentrated in vacuo. The residue was dissolved in EtOAc (50 ml), concentrated aqueous NaHCO3 solution (40 ml) was added and the mixture was stirred vigorously for 1 h. Subsequently, the organic phase was separated, dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish solid (1.20 g); MS-(+)-ion: M+1=312.0.

Workup

  1. customcan be obtained
  2. concentrationThen the mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (50 ml)
  4. additionconcentrated aqueous NaHCO3 solution (40 ml) was added
  5. stirringthe mixture was stirred vigorously for 1 h
  6. customSubsequently, the organic phase was separated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16567cd1796644b187f7a04b35562c9c
Source dataset
uspto-grants-2012_10
Patent number
US08278325B2

Reaction notes

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