2,6-Dimethylaniline → 3-Butyryl-4-(2,6-dimethylphenylamino)-8-methylquinoline

HRID 1382348Notes

Reaction equation

HRID 1382348 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]=[C:22]([CH3:26])[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[C:22]([CH3:26])=[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 68962,6-DimethylanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 104045403-Butyryl-4-(2,6-dimethylphenylamino)-8-methylquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (2.48 g, 10 mmol) and 2,6-dimethylaniline (1.85 ml, 15 mmol) in dioxan (10 ml) were heated at reflux for 30 minutes, then the solvent evaporated and the product converted to free base. Recrystallisation from aqueous ethanol gave 3-butyryl-4-(2,6-dimethylphenylamino)-8-methylquinoline, m.p. 100°-101°.

Workup

  1. temperatureat reflux for 30 minutes
  2. customthe solvent evaporated
  3. customRecrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-43d6cbab61334cac968be676fcb6bfdc
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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