3-Chloro-4-fluoroaniline → 4-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrile

HRID 548442Notes

Reaction equation

HRID 548442 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].[Cl: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>[Cl: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 97083-Chloro-4-fluoroanilineHCID 111399754-Chloro-7-methoxy-6-nitroquinoline-3-carbonitrile

Product 1

HCID 108940424-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-nitro-quinoline-3-carbonitrileYield 48.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 30156371-MethoxyethanolSolvent

Procedure

A mixture of 4.4 g (16.7 mmol) of 4-chloro-7-methoxy-6-nitro-quinoline-3-carbonitrile and 2.67 g (18.3 mmol) of 3-chloro-4-fluoro aniline in 110 ml of methoxyethanol was refluxed under nitrogen for 4 hours. The reaction mixture was diluted with ethyl acetate and wash with sodium bicarbonate solution and sodium chloride solution. The organic layer was dried over sodium sulfate and then the solvent was removed under vacuum. The residue was chromatographed on silica gel eluting with mixture of ethyl acetate and methanol to give 3 g yellow solid: mass spectrum (electrospray, m/e): 372.9.

Workup

  1. temperaturewas refluxed under nitrogen for 4 hours
  2. washwash with sodium bicarbonate solution and sodium chloride solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent 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-bf09d8a3b5db4ddea2556b6bf3fa2bcf
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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