Nitric Acid → N-(2-bromo-6-nitrophenyl)acetamide

HRID 2306252Notes

Reaction equation

HRID 2306252 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([O:12]C(=O)C)(=O)[CH3:10].[N+:16]([O-])([OH:18])=[O:17]>O>[C:9]([NH:4][C:3]1[C:5]([N+:16]([O-:18])=[O:17])=[CH:6][CH:7]=[CH:8][C:2]=1[Br:1])(=[O:12])[CH3:10]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 119922-Bromoaniline

Product 1

HCID 4643062N-(2-bromo-6-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
6 °C

Procedure

2-Bromoaniline (15 g, 87.2 mmol) was dissolved in acetic anhydride (76 mL, 0.610 mol) and cooled to 6° C. HNO3 (11 mL, 0.174 mol) was added dropwise and reaction mixture was stirred for 18 hours at 6° C. The reaction mixture was poured into H2O and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was crystallized from EtOAc—hexane, to yield the above-titled compound.

Workup

  1. customreaction mixture
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from EtOAc—hexane

Sources & evidence

ORD record
ord-2cc817ca304449fb8d6ae0f6509323b7
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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