2-Ethylaniline → 3-Butyryl-4-(2-ethylphenylamino)-8-methylquinoline

HRID 1382294Notes

Reaction equation

HRID 1382294 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[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:18]([C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22])[CH3:19]>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:22][C:21]1[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=1[CH2:18][CH3:19])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 113572-EthylanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 102462013-Butyryl-4-(2-ethylphenylamino)-8-methylquinolineYield 71.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (2.48 g, 10 mmol), 2-ethylaniline (1.85 ml, 15 mmol) and 1,4-dioxan (10 ml) were stirred at room temperature overnight then heated at reflux for 30 minutes. The solvent was evaporated, the residue converted to free base and recrystallised from aqueous ethanol to give 3-butyryl-4-(2-ethylphenylamino)-8-methylquinoline (2.38 g), m.p. 117°-119°.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 30 minutes
  3. customThe solvent was evaporated
  4. customrecrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-f83404ea5dfd4eabb45a72a057d5fcce
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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