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

HRID 420469

Reaction equation

HRID 420469 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-])=O)[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]([NH2:10])[CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 230940734'-bromo-N-methyl-2'-aminobenzanilideYield 107.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Dissolving 6.8 g (29 mmol) 4-bromo-N-methyl-2-nitroaniline obtained in the above step (1) into 20 milliliter of pyridine, further adding 5.0 g (35 mmol) benzoyl chloride, the resultant solution was refluxed with heating at the temperature of 90° C. under an atmosphere of argon gas for 7 hours. After completing the reaction, 200 milliliter of ethyl acetate was added and the resultant solution was washed with 10% HCL, with 10% K2CO3 and with a saturated solution of sodium chloride and then, dried with the use of magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure and the residue was refined with silicagel column chromatography (hexane:ethyl acetate=10:1 at primary stage→2:1 from middle stage) resultantly obtaining 9.5 g of 4′-bromo-N-methyl-2′-amino-benzanilide as greenish white solids (yield: 96%).

Workup

  1. additionwas added
  2. washthe resultant solution was washed with 10% HCL, with 10% K2CO3 and with a saturated solution of sodium chloride
  3. dry with materialdried with the use of magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-ff64d971624641f98047a4dfb26436a7
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Linked notes

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