Phosphorus oxychloride → 1-chloro-3-phenylisoquinoline

HRID 2292119Notes

Reaction equation

HRID 2292119 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Cl:19][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 6096143-Phenylisoquinoline

Product 1

HCID 119836901-chloro-3-phenylisoquinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Phenylisoquinoline (5 g) was dissolved in dry toluene (250 ml) and phosphorus oxychloride (16.52 g) was added and the mixture was heated at reflux for 48 hr, more phosphorus oxychloride (4 g) being added after 24 hr. The solvent was removed in vacuo to give 1-chloro-3-phenylisoquinoline as an oil which solidified on standing (4 g), characterised by its nmr spectrum. (A small portion was recrystallised from methanol, m.pt. 75°-77°).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 48 hr
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-016b2b74af324dfabbb27fecea12c013
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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