Nitric Acid → N-(4-Nitro-2-phenoxyphenyl)acetamide

HRID 1076451

Reaction equation

HRID 1076451 reaction equation
C1(OC2C=CC=CC=2[N+:14]([O-:16])=[O:15])C=CC=CC=1.O(C1C=CC=CC=1N)C1C=CC=CC=1.[O:31]([C:38]1[CH:47]=[CH:46][CH:45]=[CH:44][C:39]=1[NH:40][C:41](=[O:43])[CH3:42])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[N+]([O-])(O)=O>C(O)(=O)C>[N+:14]([C:46]1[CH:45]=[CH:44][C:39]([NH:40][C:41](=[O:43])[CH3:42])=[C:38]([O:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:47]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 16661Benzene, 1-nitro-2-phenoxy-HCID 75899Benzenamine, 2-phenoxy-HCID 8970802-Phenoxyacetanilide2×

Product 1

HCID 21536772N-(4-Nitro-2-phenoxyphenyl)acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

o-Nitrophenyl phenyl ether was reduced catalytically to o-phenoxyaniline, m. 43°-5°, which was acetylated to 2'-phenoxyacetanilide, m. 82°-4°. Yields from both reactions were essentially quantitative. The 2'-phenoxy-acetanilide was dissolved in acetic acid and treated at 60°-80° with red fuming nitric acid to produce a 60-70% yield of 4'-nitro-2'-phenoxy-acetanilide, m. 176°-183°. This was deacetylated by refluxing with methanolic hydrochloric acid to 4-nitro-2-phenoxyaniline, m. 116°-8°. The yield was 99% of theoretical.

Workup

  1. custom43°-5°, which
  2. custom82°-4°
  3. customYields from both reactions

Sources & evidence

ORD record
ord-ce464954457241a680b969b2492d6c21
Source dataset
uspto-grants-1976_05
Patent number
US03957489

Linked notes

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