Nitric Acid → N-(4-bromo-2-nitrophenyl)acetamide

HRID 581948Notes

Reaction equation

HRID 581948 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:3].[N+:12]([O-])([OH:14])=[O:13]>CS(O)(=O)=O>[C:2]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 76834'-Bromoacetanilide

Product 1

HCID 136690N-(4-bromo-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-bromoacetanilide (20 g, 93.4 mmol) in methanesulfonic acid is cooled to 10° C. Conc. nitric acid (12.6 ml) is added and the mixture is stirred at 40° C. for 2 hours. The mixture is poured into ice-water. The product is filtered off, washed with water and dried. Yield: 23.59 g (97%). Mp 99-100° C.

Workup

  1. filtrationThe product is filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-8d0de64f9359453cae0c0c6038f3b65f
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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