O-Toluidine → HCID 54058840, compound

HRID 1419882Notes

Reaction equation

HRID 1419882 reaction equation
[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1Cl)=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:4])[CH2:2][CH3:3].[NH2:22][C:23]1[C:24]([CH3:29])=[CH:25][CH:26]=[CH:27][CH:28]=1>C(#N)C>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 53943659HCID 53943659, compound

Product 1

HCID 54058840HCID 54058840, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Propanoyl-4-chloro-8-(3-methylthiopropoxy)quinoline (1.2 g, 3.71 mmol) and o-toluidine (0.795 g, 7.42 mmol) was refluxed in acetonitrile (18 ml) for 100 min. The solvent was evaporated and the residue was purified by column chromatography (methylene chloride:methanol 100:3). 1.45 g (99%) of the title compound was obtained.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by column chromatography (methylene chloride:methanol 100:3)

Sources & evidence

ORD record
ord-6817bc8fad3e41eb8446b1dd34c254ac
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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