4-Amino-2,6-difluorophenol → 3-Butyryl-4-(3,5-difluoro-4-hydroxyphenylamino)-8-methoxyquinoline

HRID 1885182Notes

Reaction equation

HRID 1885182 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1Cl)=[CH:23][CH:22]=[CH:21][C:20]=2[O:27][CH3:28])(=[O:15])[CH2:12][CH2:13][CH3:14]>O1CCOCC1>[C:11]([C:16]1[CH:17]=[N:18][C:19]2[C:24]([C:25]=1[NH:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([OH:10])=[C:4]([F:9])[CH:5]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[O:27][CH3:28])(=[O:15])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 27787644-Amino-2,6-difluorophenolHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 100447813-Butyryl-4-(3,5-difluoro-4-hydroxyphenylamino)-8-methoxyquinolineYield 27.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,6-Difluoro-4-aminophenol (1.49 g, 5.65 mmol) and 3-butyryl-4-chloro-8-methoxyquinoline (1.23 g, 8.48 mmol) in dioxan (50 ml) were refluxed under nitrogen for 2.5 hours. The solvent was evaporated and the product was converted to the free base, purified by flash chromatography (silica, methanol-ammonia/chloroform), triturated with methanol, filtered, washed and dried to give the title compound (0.58 g), m.p. 274°-5° (dec).

Workup

  1. customThe solvent was evaporated
  2. custompurified by flash chromatography (silica, methanol-ammonia/chloroform)
  3. customtriturated with methanol
  4. filtrationfiltered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-3774303288f2421d8830e83b5d3f4248
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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