Triphenylphosphane dichloride → 7-Chloro-4-methylisoquinoline

HRID 223144

Reaction equation

HRID 223144 reaction equation
O[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:12])=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[Cl-:13].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Cl:13][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:12])=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 13797396Triphenylphosphane dichlorideHCID 205232214-Methylisoquinolin-7-ol

Product 1

HCID 205232237-Chloro-4-methylisoquinoline

Procedure

A mixture of 15.9 g. (0.1 mole) of 7-hydroxy-4-methylisoquinoline and 41.7 g. (0.125 mole) of triphenylphosphine dichloride is heated to 230° C. for four hours, cooled, and partitioned between chloroform and concentrated hydrochloric acid. The aqueous phase is neutralized with ammonium hydroxide and extracted with chloroform to yield 7-chloro-4-methylisoquinoline.

Workup

  1. additionA mixture of 15.9 g
  2. temperaturecooled
  3. custompartitioned between chloroform and concentrated hydrochloric acid
  4. extractionextracted with chloroform

Sources & evidence

ORD record
ord-7610aea6821a4115b13fbaa01e4191c3
Source dataset
uspto-grants-1982_10
Patent number
US04352809

Linked notes

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