Nitric Acid → N-(2-nitro-4-phenoxy-phenyl)acetamide

HRID 1466470Notes

Reaction equation

HRID 1466470 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:18]([O-])([OH:20])=[O:19]>>[N+:18]([C:10]1[CH:9]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:13]=[CH:12][C:11]=1[NH:14][C:15](=[O:17])[CH3:16])([O-:20])=[O:19]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 80579N-(4-Phenoxyphenyl)acetamide

Product 1

HCID 3828525N-(2-nitro-4-phenoxy-phenyl)acetamide

Conditions

Temperature
-15 °C

Procedure

N-(4-phenoxy-phenyl)-acetamide (1.00 g, 4.03 mmol) prepared in Step A was dissolved in fuming nitric acid (2 mL), and the mixture was stirred for 2 h at −15° C. After completion of the reaction, the reaction mixture was poured into 100 mL of ice water, which was then extracted with ethyl acetate. The extracted organic solution was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (0.67 g, 2.33 mmol).

Workup

  1. customAfter completion of the reaction
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe extracted organic solution was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4e2860ca5f2b45109f1b46d7973998c3
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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