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

HRID 1472177Notes

Reaction equation

HRID 1472177 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-8897a59a956b4ad4ba376f07ad32ca9f
Source dataset
uspto-grants-2015_04
Patent number
US09012472B2

Reaction notes

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