2-Chloroaniline → HCID 9997295, compound

HRID 1382349Notes

Reaction equation

HRID 1382349 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][CH:23]=[CH:22][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[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=1[Cl: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 72402-ChloroanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 9997295HCID 9997295, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (2.48 g, 10 mmol) and 2-chloroaniline (1.6 ml, 15 mmol) in dioxan (10 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-(2-chlorophenylamino)-8-methylquinoline (1.53 g), m.p. 130°-131°.

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-4fedb07699c843c88150b3cb608e388d
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

Loading…