Stannous chloride dihydrate → Methyl 3-Amino-4-chlorobenzoate
Reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1.O.O.Cl[Sn]Cl>C(O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([NH2:11])[CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-Chloro-3-nitro-benzoic acid methyl ester (5.0 g, 23.19 mmol) in 100 ml of ethanol was added SnCl2.2H2O (26.0 g, 115.96 mmol) and the reaction mixture was heated at 80° C. for 2 h. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure. Water (100 mL) was added, basified the reaction mixture with NaOH solution and extracted with hot EtOAc (3×250 mL).
Workup
- customAfter the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure
- additionWater (100 mL) was added
- extractionextracted with hot EtOAc (3×250 mL)
Sources & evidence
- ORD record
- ord-fed5244c70f649ffb1250d4b28952243
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088791B2
Reaction notes
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