3-Bromo-4-fluoroaniline → 4-[(3-Bromo-4-fluorophenyl)amino]7-methoxy-6-nitro-quinoline-3-carbonitrile

HRID 379141Notes

Reaction equation

HRID 379141 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:17]#[N:18].[Br:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][C:26]=1[F:27])[NH2:23]>COC(O)C.C(OCC)(=O)C>[Br:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:17]#[N:18])[CH:24]=[CH:25][C:26]=1[F:27]

Participants

5

Reactant 2

HCID 27792863-Bromo-4-fluoroanilineHCID 111399754-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

Product 1

HCID 224666584-[(3-Bromo-4-fluorophenyl)amino]7-methoxy-6-nitro-quinoline-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 30156371-MethoxyethanolSolvent

Procedure

A mixture of 3.52 g (9.7 mmol) of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile and 2.0 g (10.7 mmol) of 3-bromo-4-fluoro aniline in 150 ml of methoxyethanol was refluxed under nitrogen for 5.5 hours. The reaction mixture was diluted with ethyl acetate and wash with sodium bicarbonate solution and sodium chloride solution. The organic layer was dried with sodium sulfate and then solvent was removed under vacuum. The residue was chromatographed on silica gel eluting with mixture of ethyl acetate and hexane to give the title compound.

Workup

  1. temperaturewas refluxed under nitrogen for 5.5 hours
  2. washwash with sodium bicarbonate solution and sodium chloride solution
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. customsolvent was removed under vacuum
  5. customThe residue was chromatographed on silica gel eluting with mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f05aaaf6834d4fe3a7b64d42a92342e8
Source dataset
uspto-grants-2001_10
Patent number
US06297258B1

Reaction notes

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