Phenol, 4-amino-2-fluoro- → 3-Butyryl-4-(3-fluoro-4-hydroxyphenylamino)-8-methoxyquinoline

HRID 1885165Notes

Reaction equation

HRID 1885165 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[OH:9].[C:10]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:24]=1Cl)=[CH:22][CH:21]=[CH:20][C:19]=2[O:26][CH3:27])(=[O:14])[CH2:11][CH2:12][CH3:13]>O1CCOCC1>[C:10]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:24]=1[NH:8][C:6]1[CH:5]=[CH:4][C:3]([OH:9])=[C:2]([F:1])[CH:7]=1)=[CH:22][CH:21]=[CH:20][C:19]=2[O:26][CH3:27])(=[O:14])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 2735918Phenol, 4-amino-2-fluoro-HCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 104058563-Butyryl-4-(3-fluoro-4-hydroxyphenylamino)-8-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Fluoro-4-aminophenol (0.8 g, 6 mmol) and 3-butyryl-4-chloro-8-methoxyquinoline (1.5 g, 5.7 mmol) were heated together under reflux in 1,4-dioxan (50 ml) for 1 hour. The solvent was evaporated and the residue was dissolved in dichloromethane, washed with water, sodium hydrogen oarbonate solution and brine then dried and evaporated. The residue was recrystallised from methanol-water to afford 3-butyryl-4-(3-fluoro-4-hydroxyphenylamino)-8-methoxyquinoline, m.p. 266°-268°.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water, sodium hydrogen oarbonate solution and brine
  4. customthen dried
  5. customevaporated
  6. customThe residue was recrystallised from methanol-water

Sources & evidence

ORD record
ord-d7eec50ed22d43b9851b826f16c044be
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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