Methanol → HCID 20468233, compound

HRID 1903228Notes

Reaction equation

HRID 1903228 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([S:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:6][CH:5]=1)([OH:3])=[O:2].S(Cl)([Cl:28])=O.[CH3:30]O>>[ClH:28].[CH3:24][N:23]([CH3:25])[CH2:22][CH2:21][S:20][C:11]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([O:3][CH3:30])=[O:2])=[CH:5][CH:6]=2)=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 13200302HCID 13200302, compound

Product 1

HCID 20468233HCID 20468233, compound

Procedure

3-(p-Carboxyphenyl)-2-(2-dimethylaminoethylthio)quinoline (0.7 g.) was added to a solution of thionyl chloride (1.5 ml.) in methanol (20 ml.) at 0°. The mixture was stirred at ambient temperature for 16 hr., and the solvent then evaporated. The solid residue was crystallised from methanol-ethyl acetate to give 2-(2-dimethylaminoethylthio)-3-(p-methoxycarbonylphenyl)quinoline hydrochloride, m.p. 224-5°.

Workup

  1. custom, and the solvent then evaporated
  2. customThe solid residue was crystallised from methanol-ethyl acetate

Sources & evidence

ORD record
ord-19050a81e94644429e3c746a0c6565e7
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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