4-Amino-3-nitrobenzonitrile → 3,4-Diaminobenzonitrile
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:7]#[N:8])([O-])=O.[BH4-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:7]#[N:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
3-Nitro-4-amino-benzonitrile (4.38 g) was dissolved in ethanol (600 ml) and added with stannous chloride dihydrate (34.6 g) and the whole was heated to 60° C. Sodium borohydride (366 mg) was gradually added thereto and the whole was stirred overnight at 60° C. After completion of the reaction, the resultant was filtrated through Celite and the filtrate was subjected to distillation of the solvent under reduced pressure. The residue was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was allowed to recrystallize (hexane/ethyl acetate), thereby obtaining the subject compound (2.56 g) as a brown crystal.
Workup
- customAfter completion of the reaction
- filtrationthe resultant was filtrated through Celite
- distillationthe filtrate was subjected to distillation of the solvent under reduced pressure
- dissolutionThe residue was dissolved in chloroform
- washwashed with a saturated aqueous sodium hydrogen carbonate solution
- dry with materiala saturated saline solution, and then dried with anhydrous sodium sulfate
- filtrationAfter filtration
- distillationthe solvent was distilled off under reduced pressure
- customto recrystallize (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-1f803bd36ec147aabafd3c08e0b31a1e
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932281B2
Reaction notes
Loading…