HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitric Acid → N-(4-Nitro-2-phenoxyphenyl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitric Acid | HCID 944 | — |
| Reactant | 2-Nitrophenyl phenyl ether | HCID 16661 | — |
| Reactant | Benzenamine, 2-phenoxy- | HCID 75899 | — |
| Reactant | 2-Phenoxyacetanilide | HCID 897080 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | N-(4-Nitro-2-phenoxyphenyl)acetamide | HCID 21536772 | 60% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US03957489 |
| Source dataset | uspto-grants-1976_05 |
| ORD ID | ord-ce464954457241a680b969b2492d6c21 |
| Source note | uspto-grants-1976_05 |