Thionyl Chloride → 3-(Chloromethyl)-9h-pyrido[3,4-b]indole

HRID 1919507Notes

Reaction equation

HRID 1919507 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.S(Cl)([Cl:18])=O>>[Cl:18][CH2:2][C:3]1[N:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 53533383-Hydroxymethyl-beta-carboline

Product 1

HCID 201484093-(Chloromethyl)-9h-pyrido[3,4-b]indole

Procedure

The 3-(hydroxymethyl)-β-carboline was added to an excess (3 grams) of thionyl chloride and the mixture was refluxed for 1 hour. The excess thionyl chloride was then evaporated and the obtained residue was crystallized from hexane. 2.5 grams of 3-(chloromethyl)-β-carboline was obtained.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customThe excess thionyl chloride was then evaporated
  3. customthe obtained residue was crystallized from hexane

Sources & evidence

ORD record
ord-5d11e22d74824925ab9ddf3de0b4e743
Source dataset
uspto-grants-2012_05
Patent number
US08168639B2

Reaction notes

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