2,4-Dichloroaniline → 3-Butyryl-4-(2,4-dichlorophenylamino)-8-methylquinoline

HRID 1382347Notes

Reaction equation

HRID 1382347 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].[Cl:18][C:19]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:20]=1[NH2:21]>O1CCOCC1>[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][C:24]([Cl:26])=[CH:25][C:19]=1[Cl: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 111232,4-DichloroanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 102487513-Butyryl-4-(2,4-dichlorophenylamino)-8-methylquinolineYield 60.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (2.48 g, 10 mmol), 2,4-dichloroaniline (2.43 g, 15 mmol) and 1,4-dioxan (10 ml) were stirred at room temperature overnight then heated at reflux for 30 minutes. The hydrochloride salt was filtered off, converted to free base, triturated with ethanol and recrystallised from ethyl acetate to give 3-butyryl-4-(2,4-dichlorophenylamino)-8-methylquinoline (2.26 g), m.p. 169°-170°.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 30 minutes
  3. filtrationThe hydrochloride salt was filtered off
  4. customtriturated with ethanol
  5. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-206c03c5d01a4ed7a0d41a53cf8c2b09
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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