2-Methoxy-5-Methylaniline → 3-Butyryl-4-(2-methoxy-5-methylphenylamino)-8-methylquinoline

HRID 1382351Notes

Reaction equation

HRID 1382351 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]([CH3:27])=[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]([CH3:27])[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 84452-Methoxy-5-MethylanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 100663503-Butyryl-4-(2-methoxy-5-methylphenylamino)-8-methylquinolineYield 53.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (1.77 g, 7.14 mmol) and 2-methoxy-5-methylaniline (1.47 g, 10.7 mmol) in dioxan (10 ml) were heated at reflux for 30 minutes, then evaporated and converted to free base. Recrystallisation from methanol and then from ethyl acetate/petroleum ether gave 3-butyryl-4-(2-methoxy-5-methylphenylamino)-8-methylquinoline (1.32 g), m.p. 136°-138°.

Workup

  1. temperatureat reflux for 30 minutes
  2. customevaporated
  3. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-a16ffb9f56b64966a93f300eb70169df
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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