Pyridine → N-(3-bromo-5-nitrophenyl)acetamide

HRID 1028102

Reaction equation

HRID 1028102 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1)[NH2:5].N1C=CC=CC=1.[C:18](Cl)(=[O:20])[CH3:19]>ClCCl.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:18](=[O:20])[CH3:19])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 44535ar-Bromo-ar-nitrobenzenamine

Product 1

HCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Bromo-5-nitroaniline (6.45 g, 29.7 mmol) was dissolved in dichloromethane (149 mL) and pyridine (2.88 mL, 35.7 mmol). The solution was cooled to 0° C. and then, acetyl chloride (2.325 mL, 32.7 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1 hour. The reaction was diluted with water and dichloromethane and the organic phase was dried over sodium sulfate and was concentrated to dryness. N-(3-bromo-5-nitrophenyl)acetamide was isolated as a beige powder (7.86 g, 30 mmol, 100%) and was of sufficient purity to carry forward without further purification.

Workup

  1. dry with materialthe organic phase was dried over sodium sulfate
  2. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-70ec7c4f20d74ae5b7511b8de2beb47a
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Linked notes

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