Nitric Acid → N-(5-Bromo-4-methoxy-2-nitrophenyl)acetamide

HRID 2406415Notes

Reaction equation

HRID 2406415 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([CH3:11])=[O:10])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[N+:14]([O-])([OH:16])=[O:15].O>C(OC(=O)C)(=O)C.C(O)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([CH3:11])=[O:10])[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 244158N-(3-bromo-4-methoxyphenyl)acetamide

Product 1

HCID 235991N-(5-Bromo-4-methoxy-2-nitrophenyl)acetamideYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
5 °C

Procedure

To a cold (5° C.) solution of 3.36 g (13.8 mmol) of 2-Bromo-4-acetaminoanisole in 5 mL of acetic anhydride and 10 mL of acetic acid, was added dropwise 0.9 mL (13.8 mmol) of concentrate nitric acid. The resulting solution was stirred at 5° C. for 3 h, poured into 90 mL of water, stirred, and filtered to collect the solid (the desired product). The solid was washed twice with cold water, dried under vacuo at 100° C., crystallized from chloroform to give 3.26 g (82% yield) of pure compound 6. 1H NMR (CDCl3) δ 10.2 (s, 1 H, NH), 9.09 (s, 1 H), 7.67 (s, 1 H), 3.95 (s, 3 H, OMe), 2.28 (s, 3 H, CH3).

Workup

  1. stirringstirred
  2. filtrationfiltered
  3. customto collect the solid (the desired product)
  4. washThe solid was washed twice with cold water
  5. customdried under vacuo at 100° C.
  6. customcrystallized from chloroform

Sources & evidence

ORD record
ord-8f96ddcec83b46f88f7914e00520eeb5
Source dataset
uspto-grants-2014_08
Patent number
US08809368B2

Reaction notes

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