4-Chloro-2-toluidine → 3-Butyryl-4-(4-chloro-2-methylphenylamino)-8-methylquinoline

HRID 1382350Notes

Reaction equation

HRID 1382350 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]=[CH:24][C:22]([NH2:23])=[C:21]([CH3:26])[CH:20]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:23][C:22]1[CH:24]=[CH:25][C:19]([Cl:18])=[CH:20][C:21]=1[CH3:26])=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 72514-Chloro-2-toluidineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 117255953-Butyryl-4-(4-chloro-2-methylphenylamino)-8-methylquinolineYield 41.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (1.24 g, 5 mmol) and 4-chloro-2-methylaniline (1.06 g, 7.5 mmol) in dioxan (5 ml) were heated at reflux for 30 minutes, then allowed to cool. The product was filtered off, converted to free base, and recrystllised from methanol, to give 3-butyryl-4-(4-chloro-2-methylphenylamino)-8-methylquinoline (0.73 g), m.p. 166°-167°.

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureto cool
  3. filtrationThe product was filtered off

Sources & evidence

ORD record
ord-149149ffb8484c6483b693da381d44cf
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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