4-Fluoro-2-methylaniline → 3-Butyryl-4-(4-fluoro-2-methylphenylamino)-8-(2-methylthioethoxy)quinoline

HRID 743110Notes

Reaction equation

HRID 743110 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[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4].[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([CH3:30])[CH:24]=1>C(#N)C>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:27][C:26]1[CH:28]=[CH:29][C:23]([F:22])=[CH:24][C:25]=1[CH3:30])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH2:18][CH2:19][S:20][CH3:21])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 679824-Fluoro-2-methylanilineHCID 545624293-Butyryl-4-chloro-8-(2-methylthioethoxy)quinoline

Product 1

HCID 544182293-Butyryl-4-(4-fluoro-2-methylphenylamino)-8-(2-methylthioethoxy)quinolineYield 11.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-butyryl-4-chloro-8-(2-methylthioethoxy)quinoline (2.75 g, 8.2 mmol) and 4-fluoro-2-methylaniline (1.34 g, 10.7 mmol) in acetonitrile (20 ml) was refluxed for 8 h. The solution was cooled and 1.52 g crystallized product was filtered off. The filtrate was evaporated and chromatographed (SiO2 ; CH2Cl2 :MeOH 95:5) yielding 0.4 g of the desired product. Total yield: 1.92 g (57%).

Workup

  1. temperaturewas refluxed for 8 h
  2. temperatureThe solution was cooled
  3. custom1.52 g crystallized product
  4. filtrationwas filtered off
  5. customThe filtrate was evaporated
  6. customchromatographed (SiO2 ; CH2Cl2 :MeOH 95:5)

Sources & evidence

ORD record
ord-670d0b1eddae43e2a8f3729c91151a9a
Source dataset
uspto-grants-1996_09
Patent number
US05556863

Reaction notes

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