2,5-Dimethoxyaniline → 3-Butyryl-4-(2,5-dimethoxyphenylamino)-8-methylquinoline

HRID 1382292Notes

Reaction equation

HRID 1382292 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][O:19][C:20]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:21]=1[NH2:22]>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]=[C:24]([O:27][CH3:28])[CH:25]=[CH:26][C:20]=1[O:19][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 76132,5-DimethoxyanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 100901843-Butyryl-4-(2,5-dimethoxyphenylamino)-8-methylquinolineYield 29.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (2.48 g, 10 mmol), 2,5-dimethoxyaniline (3.06 g, 20 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 and recrystallised from aqueous ethanol to give 3-butyryl-4-(2,5-dimethoxyphenylamino)-8-methylquinoline (1.07 g), m.p. 115°-116°.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 30 minutes
  3. filtrationThe hydrochloride salt was filtered off
  4. customrecrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-494f64f3f89d49a2b06d2f176656c306
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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