Nitric Acid → N-(2-nitro-4-propanoylphenyl)acetamide

HRID 626233Notes

Reaction equation

HRID 626233 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].[N+:15]([O-])([OH:17])=[O:16].O>OS(O)(=O)=O>[N+:15]([C:7]1[CH:6]=[C:5]([C:1](=[O:4])[CH2:2][CH3:3])[CH:10]=[CH:9][C:8]=1[NH:11][C:12](=[O:14])[CH3:13])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 85655N-[4-(1-oxopropyl)phenyl]acetamide

Product 1

HCID 59569038N-(2-nitro-4-propanoylphenyl)acetamideYield 50%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of N-(4-propionylphenyl)acetamide (1.91 g, 10 mmol) in 20 mL of concentrated H2SO4 was added 2 mL 98% HNO3 over 10 minutes while maintain the temperature at −10° C. After stirring for 0.5 h, the mixture was poured into 100 mL of cold water. The precipitate was collected by filtration and washed with water to give the crude product (1.18 g, 50%), which was used directly in the next step.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-a2b8cf2a46fe4d2d8ecb911e4e67f785
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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