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

HRID 1730271Notes

Reaction equation

HRID 1730271 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 addedportionwise 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. customwas addedportionwise to a stirred 0° C.
  2. customto rise slowly to 25° C
  3. additionSubsequently the reaction mixture was poured into 100 ml
  4. customdid not crystallize
  5. extractionThe mixture was extracted with ether
  6. customevaporated

Sources & evidence

ORD record
ord-67c1e726883b4ca8b1f8d218655bb15a
Source dataset
uspto-grants-1976_11
Patent number
US03992378

Reaction notes

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