Thionyl Chloride → 1-Methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline

HRID 1088786Notes

Reaction equation

HRID 1088786 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12]O)[CH2:5][CH2:4][CH2:3]1.S(Cl)([Cl:16])=O>ClCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12][Cl:16])[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15053143(1-Methyl-1,2,3,4-tetrahydroquinolin-8-yl)methanol

Product 1

HCID 150531421-Methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

1-Methyl-8-hydroxymethyl-1,2,3,4-tetrahydroquinoline (0.89 g) was dissolved in dichloromethane (30 ml), and thionyl chloride (1.09 ml) was added thereto, and the mixture was stirred for 2 hours at 45° C. After distilling off the solvent, n-hexane was added to the residue, and the solvent was distilled off under reduced pressure to give 1-methyl-8-chloromethyl-1,2,3,4-tetrahydroquinoline (1.1 g).

Workup

  1. distillationAfter distilling off the solvent, n-hexane
  2. additionwas added to the residue
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9b4e89eb7660459282e501acd1261d69
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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