Water → HCID 12851845, compound

HRID 1156902Notes

Reaction equation

HRID 1156902 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18]O)[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:21].O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18][Cl:21])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24819Phosphorus pentachlorideHCID 128518441-(4-Methylphenyl)-5-hydroxymethylisoquinoline

Product 1

HCID 12851845HCID 12851845, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(4-Methylphenyl)-5-hydroxymethylisoquinoline (7.5 g) was dissolved in 80 ml of chloroform, and 12.5 g of phosphorus pentachloride was added under ice cooling. The mixture was stirred at room temperature for 1 hour, and 100 ml of water was added. The mixture was stirred for 30 minutes, and neutralized with potassium carbonate. The chloroform layer was washed in water, and dried. The solvent was distilled off, and the residue was recrystallized from methanol to afford 8.6 g of 1-(4-methylphenyl)-5-chloromethylisoquinoline as slightly yellow prisms having a melting point of 119.8° to 120.1° C.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. washThe chloroform layer was washed in water
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-0fc9aba366a44012ba503b0dcd725e8f
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

Loading…