O-Toluidine → 3-Butyryl-4-(2-methylphenylamino)-8-methylquinoline

HRID 1382288Notes

Reaction equation

HRID 1382288 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].[CH3:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21]>O1CCCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:21][C:20]1[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=1[CH3:18])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 103360373-Butyryl-4-(2-methylphenylamino)-8-methylquinolineYield 20.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (4.95 g, 20 mmol), 2-methylaniline (4.27 ml, 40 mmol) and tetrahydrofuran (20 ml) were heated at reflux for 30 minutes, the solvent evaporated and the residue triturated with ethyl acetate/ethanol. The hydrochloride salt was filtered off, converted to free base and recrystallised from ethyl acetate/petroleum ether then from aqueous methanol, to give 3-butyryl-4-(2-methylphenylamino)-8-methylquinoline (1.3 g), m.p. 110°-112°.

Workup

  1. temperatureat reflux for 30 minutes
  2. customthe solvent evaporated
  3. customthe residue triturated with ethyl acetate/ethanol
  4. filtrationThe hydrochloride salt was filtered off
  5. customrecrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-353442b0094942998f1d0721d4f561d5
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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