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

HRID 2262440Notes

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

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

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

Sources & evidence

ORD record: ord-0eabbe7725854834b1c9f24ab18533ae
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851071B2

Reaction notes

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