4-Amino-m-cresol → 3-Butyryl-4-(4-hydroxy-2-methylphenylamino)-8-fluoroquinoline

HRID 1885170Notes

Reaction equation

HRID 1885170 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[F:17])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=1[CH3:26]>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=1[CH3:26])=[CH:13][CH:12]=[CH:11][C:10]=2[F:17])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 178194-Amino-m-cresolHCID 104448833-Butyryl-4-chloro-8-fluoroquinoline

Product 1

HCID 100427563-Butyryl-4-(4-hydroxy-2-methylphenylamino)-8-fluoroquinolineYield 50.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-butyryl-4-chloro-8-fluoroquinoline (1.75 g, 7 mmol), 4-amino-3-methylphenol (1.3 g, 10 mmol) and 1,4-dioxan (50 ml) were heated at reflux for 6.5 hours, then the solvent evaporated and the product converted to free base. Recrystallisation from methanol gave 3-butyryl-4-(4-hydroxy-2-methylphenylamino)-8-fluoroquinoline (1.2 g), m.p. 205°-207°.

Workup

  1. temperatureat reflux for 6.5 hours
  2. customthe solvent evaporated
  3. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-77dbfa8c23374342b85308553ee35733
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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