Nitric Acid → N-(2-Nitro-3-(trifluoromethyl)phenyl)acetamide

HRID 1470627Notes

Reaction equation

HRID 1470627 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[N+:15]([O-])([OH:17])=[O:16]>>[N+:15]([C:4]1[C:3]([C:2]([F:13])([F:14])[F:1])=[CH:8][CH:7]=[CH:6][C:5]=1[NH:9][C:10](=[O:12])[CH3:11])([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 9595Acetamide, N-(3-(trifluoromethyl)phenyl)-

Product 1

HCID 223112N-(2-Nitro-3-(trifluoromethyl)phenyl)acetamideYield 27.74%

Procedure

N-(3-trifluoromethyl-phenyl)-acetamide (2.8 g, 13.7 mmol) was added in small portions to the cold fuming nitric acid (10 mL) taken in a dry round bottom flask at −10° C. The reaction mixture was stirred for another 10 minutes at the same temperature then quenched with water (50 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and concentrated to dryness. The obtained residue was purified by column chromatography using 20% ethylacetate in hexane to get the title compound as yellow solid (0.9 g, 27.74%).

Workup

  1. customtaken in a dry round bottom flask at −10° C
  2. customthen quenched with water (50 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated to dryness
  6. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-a9a84559a3844ba1866367caf46c7700
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

Loading…