Ethanol → Ethyl 3-amino-2-nitrobenzoate
Reaction equation
C([NH:4][C:5]1[C:6]([N+:14]([O-:16])=[O:15])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=O)C.S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[NH2:4][C:5]1[C:6]([N+:14]([O-:16])=[O:15])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH2:22][CH3:23])=[O:9]Participants
4
Procedure
A mixture of 20.2 g of 3-acetylamino-2-nitrobenzoic acid, 11.4 g of 97% sulfuric acid and 300 ml of ethanol was stirred for 23 hours while being heat-refluxed. One-hundred milliliters of ethanol were distilled off under reduced pressure, and the residue was cooled to room temperature. Subsequently, the reaction solution was poured into 200 ml of ice water containing 19.5 g of sodium hydrogencarbonate. The crystals precipitated were separated through filtration, and were washed with water. Further, these crystals were dispersed in 30 ml of a mixed solution of ethyl acetate and hexane at a ratio of 1:2. The crystals were separated through filtration, washed with hexane, and then dried to give 18.0 g of ethyl 3-amino-2-nitrobenzoate.
Workup
- temperaturewhile being heat-refluxed
- distillationOne-hundred milliliters of ethanol were distilled off under reduced pressure
- additionSubsequently, the reaction solution was poured into 200 ml of ice water containing 19.5 g of sodium hydrogencarbonate
- customThe crystals precipitated
- customwere separated through filtration
- washwere washed with water
- additionFurther, these crystals were dispersed in 30 ml of a mixed solution of ethyl acetate and hexane at a ratio of 1:2
- customThe crystals were separated through filtration
- washwashed with hexane
- customdried
Sources & evidence
- ORD record
- ord-89255ad9db5442329111b6fd6ee63e7e
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06166219
Reaction notes
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