Pyridine → 4'-bromo-N-methyl-2'-nitrobenzanilide

HRID 1172768Notes

Reaction equation

HRID 1172768 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 2580424-Bromo-N-methyl-2-nitroaniline

Product 1

HCID 230940784'-bromo-N-methyl-2'-nitrobenzanilideYield 97.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

6.8 g (29 mmol) of 4-bromo-N-methyl-2-nitroaniline were dissolved into 20 mL of pyridine. Furthermore, 5.0 g (35 mmol) of benzoyl chloride were added, and the whole was stirred under heating at 90° C. for 7 hours in an argon atmosphere. After the completion of the reaction, 200 mL of ethyl acetate were added, and the whole was washed with 10-mass % hydrochloric acid, 10-mass % K2CO3, and a saturated sodium chloride solution, and dried with magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was purified by means of silica gel column chromatography to obtain 9.5 g of 4′-bromo-N-methyl-2′-nitro-benzanilide as a greenish white solid (96% yield).

Workup

  1. additionwere added
  2. washthe whole was washed with 10-mass % hydrochloric acid, 10-mass % K2CO3
  3. dry with materiala saturated sodium chloride solution, and dried with magnesium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-6957104583bf4b228805b5b504a65efe
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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