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

HRID 1382298Notes

Reaction equation

HRID 1382298 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 recrystallised 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
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-df9a6b26d8fc445aaee849187170158c
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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