2-Fluoroaniline → 8-Methylquinoline

HRID 1382293Notes

Reaction equation

HRID 1382293 reaction equation
C([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)CCC.FC1C=CC=CC=1N>O1CCOCC1>[CH3:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[CH:7][CH:6]=[CH:15]2

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 100376273-Butyryl-4-chloro-8-methylquinoline

Product 1

HCID 119108-MethylquinolineYield 154.3%

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-7dd50732c3ab4a888ec9b49a7d57cb04
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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