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

HRID 612133Notes

Reaction equation

HRID 612133 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-carbonitrileYield 74.1%

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-3-quinolinecarbonitrile 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 methanol to give 3 g of yellow solid: mass spectrum (electrospray, m/e): 416.8 and 418.8.

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 methanol

Sources & evidence

ORD record
ord-b9a1c9e4552b4f0ea40172a67bea4baf
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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