Stannous chloride dihydrate → 2,3-Diaminobenzoic acid methyl ester
Reaction equation
O.O.[Sn](Cl)Cl.[NH2:6][C:7]1[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]>CO>[NH2:6][C:7]1[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Tin(II)chloride dihydrate (17.25 g, 76.5 mmol) was added in one portion to methyl 2-amino-3-nitrobenzoate (5.0 g, 25.5 mmol) in methanol (100 mL) under nitrogen. The yellow mixture was vigorously stirred at 65° C. for 16 h, and the solvent was removed by rotory evaporation to near dryness. The residue was taken up in ethyl acetate and the solution was poured into a large beaker containing 1:1 ethyl acetate/NaHCO3 soln. (300 mL) and stirred 15 min. The precipitates were removed by filtration and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layers were washed with saturated NaHCO3 solution, brine, and dried (Na2SO4). Concentration gave methyl 2,3-diaminobenzoate as a deep red viscous oil 4.1 g (97%).
Workup
- customthe solvent was removed by rotory evaporation
- additionthe solution was poured into a large beaker
- additioncontaining 1:1 ethyl acetate/NaHCO3 soln
- stirring(300 mL) and stirred 15 min
- customThe precipitates were removed by filtration
- customthe organic layer was separated
- extractionThe aqueous layer was extracted twice with ethyl acetate
- washthe combined organic layers were washed with saturated NaHCO3 solution, brine
- dry with materialdried (Na2SO4)
- concentrationConcentration
Sources & evidence
- ORD record
- ord-c6eac376bb504faba1f5c18d723ea613
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394968B2
Reaction notes
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