2-Fluoroaniline → HCID 10471369, compound

HRID 1382345Notes

Reaction equation

HRID 1382345 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].[F: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[F: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 95842-FluoroanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 10471369HCID 10471369, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methylquinoline (2.48 g, 10 mmol), 2-fluoroaniline (1.45 ml, 15 mmol) and 1,4-dioxan (10 ml) were stirred at room temperature overnight then heated at reflux for 30 minutes. The hydrochloride salt was filtered off, converted to free base and recrystallised from aqueous ethanol to give 3-butyryl-4-(2-fluorophenylamino)-8-methylquinoline (2.21 g), m.p. 109°-111°.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 30 minutes
  3. filtrationThe hydrochloride salt was filtered off
  4. customrecrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-dbffc411d6384bd6ae66cc94295bfa57
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

Loading…