Reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1.[N+:17]([O-])([O:19]C(=O)C)=[O:18].[N+]([O-])(O)=O.CC1C=CC=CC=1N>>[F:8][C:9]1[CH:10]=[C:11]([CH3:16])[C:12]([NH:13][C:5]([CH3:6])=[O:7])=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=1Participants
Conditions
- Temperature
- 7 °C
Procedure
Stirred acetic anhydride, 300 mL, was cooled to about 7° C., and 25.1 grams (0.20 mole) of 4-fluoro-2-methylaniline was added dropwise during a 30 minute period. Upon completion of addition, the reaction mixture was stirred at about 10° C. for an additional 15 minutes. In a separate reaction vessel, acetyl nitrate was prepared by the dropwise addition of 14.9 mL of 90% nitric acid to 30 mL of stirred, cold (0°-15° C.) acetic anhydride during a 15 minute period. The so-prepared acetyl nitrate was cooled to about -5° C., placed in a dropping funnel, and added dropwise during a 30 minute period to the 2-methylaniline solution. Upon completion of addition, the reaction mixture was stirred an additional 5 hours. After this time the reaction mixture was poured into 400 grams of ice. The resultant solid was collected by filtration, washed with water, and dried at 60° C. under vacuum, yielding 23.0 grams of 5-fluoro-2-methylcarbonylamino-3-methylnitrobenzene, mp 167°-172° C. The NMR spectrum was consistent with the proposed structure.
Workup
- additionUpon completion of addition
- stirringof stirred
- customplaced in a dropping funnel
- additionUpon completion of addition
- stirringthe reaction mixture was stirred an additional 5 hours
- filtrationThe resultant solid was collected by filtration
- washwashed with water
- customdried at 60° C. under vacuum
Sources & evidence
- ORD record
- ord-e3c956dc6aac4315bf1090e7f781f7ff
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616718
Linked notes
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