Nitric Acid → N-(2-acetyl-6-nitrophenyl)acetamide
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:13])[CH3:12])(=[O:3])[CH3:2].OS(O)(=O)=O.[N+:19]([O-])([OH:21])=[O:20]>>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:19]([O-:21])=[O:20])[C:5]=1[NH:10][C:11](=[O:13])[CH3:12])(=[O:3])[CH3:2]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A solution of N-(2-acetyl-phenyl)-acetamide (1 g, 5.65 mmol) in conc. H2SO4 (2.8 mL, 45.2 mmol) was cooled to −20° C. and fuming nitric acid (2 mL, 33 mmol) was slowly added. The reaction mixture was warmed to 0° C. and stirred for 7 h. After completion of the starting material, the reaction mixture was quenched with water and extracted with dichloromethane (2×25 mL). The combined organic layers were washed with brine and water, then dried over anhydrous sodium sulphate and concentrated to dryness. The resulting residue was purified by column chromatography using 1% methanol in chloroform to get the title compound as yellow solid
Workup
- customAfter completion of the starting material, the reaction mixture was quenched with water
- extractionextracted with dichloromethane (2×25 mL)
- washThe combined organic layers were washed with brine and water
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated to dryness
- customThe resulting residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-de4f7412dca3426bbf7e8851b3e43989
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006454B2
Reaction notes
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