Pyridine → HCID 59455903, compound

HRID 883054Notes

Reaction equation

HRID 883054 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.N1C=CC=CC=1.[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28]>O1CCCC1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH:6][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([F:17])=[C:19]([N+:27]([O-:29])=[O:28])[CH:20]=2)=[C:4]([CH3:10])[CH:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 905494-Bromo-2,6-xylidineHCID 27833474-Fluoro-3-nitrobenzoyl chloride

Product 1

HCID 59455903HCID 59455903, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 4-bromo-2,6-dimethylaniline (15 g, 75 mmol) (commercially available) and pyridine (16.1 ml, 200 mmol) in anhydrous tetrahydrofuran (150 ml) under an atmosphere of nitrogen was added the solution of 4-fluoro-3-nitrobenzoyl chloride (Step A). The reaction mixture was stirred at ambient temperature for 8 hours. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydrogen carbonate (saturated). The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1) to give N-(4-bromo-2,6-dimethyl-phenyl)-4-fluoro-3-nitro-benzamide (27.54 g, 67% yield) which was used without further purification. LC/MS (Method A): 369 (MH+), 410 (MH++CH3CN).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-653fb6dbe5a74bee827d257080b147c7
Source dataset
uspto-grants-2012_08
Patent number
US08236828B2

Reaction notes

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