Nitric Acid → N-(4-ethyl-2-nitrophenyl)acetamide

HRID 1658052Notes

Reaction equation

HRID 1658052 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:7]1[CH:16]=[CH:15][C:10]([NH:11][C:12](=[O:14])[CH3:13])=[CH:9][CH:8]=1)[CH3:6].O>C(OC(=O)C)(=O)C.C(O)(=O)C>[N+:1]([C:9]1[CH:8]=[C:7]([CH2:5][CH3:6])[CH:16]=[CH:15][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])([O-:4])=[O:2]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 72893N-(4-Ethylphenyl)acetamide

Product 1

HCID 15919553N-(4-ethyl-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of fuming nitric acid (1.4 ml.) and acetic acid (2 ml.) was added portionwise to a stirred 0°C. solution of p-ethylacetanilide (4.0 grams) in acetic anhydride (4.2 ml.) and acetic acid (4.4 ml.). The temperature was allowed to rise slowly to 25°C. Subsequently the reaction mixture was poured into 100 ml. of water. An oil settled but did not crystallize. The mixture was extracted with ether and evaporated, leaving the 2'-nitro-4'-ethylacetanilide as a dark oil.

Workup

  1. customto rise slowly to 25°C
  2. additionSubsequently the reaction mixture was poured into 100 ml
  3. customdid not crystallize
  4. extractionThe mixture was extracted with ether
  5. customevaporated

Sources & evidence

ORD record
ord-ce0f96b43889464fa0ab035af42e9c34
Source dataset
uspto-grants-1976_06
Patent number
US03962440

Reaction notes

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