Water → 1-Isopropyl-5-chloromethylisoquinoline

HRID 1156912Notes

Reaction equation

HRID 1156912 reaction equation
[CH:1]([C:4]1[C:13]2[C:8](=[C:9]([CH2:14]O)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:18])=O.O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH:1]([C:4]1[C:13]2[C:8](=[C:9]([CH2:14][Cl:18])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 128327671-Isopropyl-5-hydroxymethylisoquinoline

Product 1

HCID 128327681-Isopropyl-5-chloromethylisoquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-iso-Propyl-5-hydroxymethylisoquinoline (6.5 g) was dissolved in 50 ml of chloroform and 6.5 ml of phosphorus oxychloride was added dropwise under ice cooling. The mixture was stirred at room temperature for 1 hour. Water (50 ml) was added to the reaction mixture, and it was made weakly alkaline with potassium carbonate. The chloroform layer was washed in water, and dried. The solvent was distilled off under reduced pressure to afford 7.1 g of 1-isopropyl-5-chloromethylisoquinoline as a colorless oil.

Workup

  1. washThe chloroform layer was washed in water
  2. customdried
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cb4e0d037d424bc588ec5211c7c820c4
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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