Nitric Acid → 2,2,2-Trifluoro-N-[2-(4-methoxy-3-nitrophenyl)ethyl]acetamide
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:4].[N+:18]([O-])([OH:20])=[O:19]>FC(F)(F)C(O)=O>[F:1][C:2]([F:16])([F:17])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([N+:18]([O-:20])=[O:19])[CH:9]=1)=[O:4]Participants
Procedure
To a solution of 30 g (0.121 mole) of the amide in 254 ml of trifluoroacetic acid at 0° under an argon atmosphere was added dropwise with stirring a solution of 7.5 ml (0.12 mole) of conc. nitric acid in 56 ml of trifluoroacetic acid. The reaction mixture was stirred at 0° for 1/2 hour and at room temperature for 2 hours. The solvents were evaporated. The residue was dissolved in ethyl acetate which was extracted with 5% hydrochloric acid, dilute sodium bicarbonate solution and brine, then dried over anhydrous magnesium sulfate and activated charcoal. After filtering, the solvents were removed to give 34.8 g (98%) of crude (2-trifluoroacetamidoethyl)-3-nitro-4-methoxybenzene which was an amber-colored solid. This material was recrystallized from 400 ml of 1:3 ethyl acetatehexane to give 25.3 g (71.5%) of the product, m.p. 92.5°-93.0°. The mother liquors were concentrated and recrystallized to give a second crop, 4.59 g (13 %), m.p. 90°-92° C.
Workup
- customThe solvents were evaporated
- dissolutionThe residue was dissolved in ethyl acetate which
- extractionwas extracted with 5% hydrochloric acid, dilute sodium bicarbonate solution and brine
- dry with materialdried over anhydrous magnesium sulfate and activated charcoal
- filtrationAfter filtering
- customthe solvents were removed
Sources & evidence
- ORD record
- ord-ee5cdb4266524e0ba3cf7c19cbceea89
- Source dataset
- uspto-grants-1983_11
- Patent number
- US04414224
Reaction notes
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