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

HRID 334485Notes

Reaction equation

HRID 334485 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[N+:9]([O-:12])(O)=[O:10].[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:12])=[O:10])[C:3]=1[NH:4][C:13](=[O:15])[CH3:14]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 119922-Bromoaniline

Product 1

HCID 4643062N-(2-bromo-6-nitrophenyl)acetamideYield 16.7%

Procedure

To a solution of 2-bromoaniline (XC) (50 g, 0.29 mol, 1 eq) in acetic anhydride (265 mL) was added dropwise nitric acid (fuming) (36.75 mL, 0.93 mol, 3.2 eq) at 0° C. and then stirred at that temperature, when the starting material was consumed, the mixture was filtered, the filtrate was poured into ice water. The aqueous phase was basified with aqueous solution of sodium bicarbonate to pH=7, then the mixture was extracted with EtOAc (30 mL×3). The organic layers were combined, dried and concentrated in vacuo to give the N-(2-bromo-6-nitrophenyl)acetamide (XCI) (12.6 g, 48.6 mmol, 16.7% yield) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ ppm 2.06 (s, 3H), 7.43 (t, J=8 Hz, 1H), 7.94 (d, J=8 Hz, 1H), 8.05 (d, J=8 Hz, 1H); ESIMS found for C8H7BrN2O3 m/z 259 (M+H).

Workup

  1. customwas consumed
  2. filtrationthe mixture was filtered
  3. additionthe filtrate was poured into ice water
  4. extractionthe mixture was extracted with EtOAc (30 mL×3)
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9284cc903d174d8ca9659694aeccf5b0
Source dataset
uspto-grants-2014_11
Patent number
US08883822B2

Reaction notes

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