2-Ethylaniline → 3-Butyryl-4-(2-ethylphenylamino)-8-(2-methylthioethoxy)quinoline

HRID 1419866Notes

Reaction equation

HRID 1419866 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:22]([C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26])[CH3:23]>C(#N)C>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:26][C:25]1[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=1[CH2:22][CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 113572-EthylanilineHCID 545624293-Butyryl-4-chloro-8-(2-methylthioethoxy)quinoline

Product 1

HCID 542565133-Butyryl-4-(2-ethylphenylamino)-8-(2-methylthioethoxy)quinolineYield 69.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-butyryl-4-chloro-8-(2-methylthioethoxy)quinoline (3.69 g, 9.84 mmol) and 2-ethylaniline (1.55 g, 12.8 mmol) in acetonitrile (20 ml) was refluxed for 6 h. The solution was evaporated. Chromatography (SiO2 ; CH2Cl2 :MeOH 97:3) gave 2.79 g (69%) of the desired product.

Workup

  1. temperaturewas refluxed for 6 h
  2. customThe solution was evaporated

Sources & evidence

ORD record
ord-eb71f54da8524dc8ba540776c03e015d
Source dataset
uspto-grants-1999_03
Patent number
US05889021

Reaction notes

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