Hydrochloric Acid → Ethyl 4-Amino-2-fluorobenzoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[F:14])[CH3:2].[Sn].Cl>O1CCCC1>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[F:14])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2-fluoro-4-nitro-benzoic acid ethyl ester (725 mg, 3.4 mmol) in tetrahydrofuran (11 ml) was treated with tin metal (807 mg, 6.8 mmol, 2 equiv.) and 6N HCl (5.4 ml). The mixture was warmed to 50° C. and stirred for 30 min. After cooling to room temperature, the solvent was evaporated. The residue was cooled to 0° C. and treated with 10% NaOH (20 ml). After stirring for a few minutes, the suspension was filtered, washing with water. The solid was dissolved in tetrahydrofuran and treated with Na2SO4. Filtration and evaporation of the solvent yielded a light yellow solid, which was purified by trituration in diisopropylether. 4-Amino-2-fluorobenzoic acid ethyl ester was obtained as a light yellow solid, 554 mg (89% yield), MS (ISP): m/e=184.1 (M+H+).
Workup
- temperatureAfter cooling to room temperature
- customthe solvent was evaporated
- temperatureThe residue was cooled to 0° C.
- additiontreated with 10% NaOH (20 ml)
- stirringAfter stirring for a few minutes
- filtrationthe suspension was filtered
- washwashing with water
- dissolutionThe solid was dissolved in tetrahydrofuran
- additiontreated with Na2SO4
- filtrationFiltration and evaporation of the solvent
- customyielded a light yellow solid, which
- customwas purified by trituration in diisopropylether
Sources & evidence
- ORD record
- ord-82bd9e69ab2c4aee89cc85c76089d936
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713996B2
Reaction notes
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