Phosphorus oxychloride → 4-[(1,7-Dichloro-3-isoquinolinyl)methylamino]phenol

HRID 647419Notes

Reaction equation

HRID 647419 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([N:13]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH3:14])[N:8]=[C:9]2O)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[C:7]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH3:14])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178482209HCID 178482209, compound

Product 1

HCID 133862264-[(1,7-Dichloro-3-isoquinolinyl)methylamino]phenol

Procedure

A mixture of 4-[N-(7-chloro-1-hydroxyisoquinolin-3-yl)-N-methylamino]phenol (4.0 g) and phosphorus oxychloride was heated under reflux for approximately 10 minutes at which stage a clear solution had been obtained. The mixture was cooled and poured into ice-water. The precipitated solid was collected and purified by column chromatography over silica gel (eluant dichloromethane/ethyl acetate; 90:10) to give 4-[N-(1,7-dichloroisoquinolin-3-yl)-N-methylamino]phenol (2.57 g) as a yellow crystalline solid mp 124° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for approximately 10 minutes at which stage a clear solution
  3. customhad been obtained
  4. temperatureThe mixture was cooled
  5. customThe precipitated solid was collected
  6. custompurified by column chromatography over silica gel (eluant dichloromethane/ethyl acetate; 90:10)

Sources & evidence

ORD record
ord-22fa555955744685ab11c7414c3f9a57
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

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