4-Ethynyl-1,2-dinitrobenzene → 1,2-Benzenediamine, 4-ethynyl- (9CI)
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]#[CH:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)([O-])=O>[OH-].[NH4+].O1CCCC1.[Zn]>[C:13]([C:6]1[CH:7]=[CH:8][C:9]([NH2:10])=[C:4]([NH2:1])[CH:5]=1)#[CH:14]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
To a rapidly stirred suspension of 4.1 g of powdered zinc in 10 ml of concentrated ammonium hydroxide was added a solution containing 1.2 g (6.3 mmoles) of 3,4-dinitroethynyl benzene dissolved in 10 ml of tetrahydrofuran. The mixture was stirred at room temperature for one-half hour at which time it was filtered by suction and the residue was washed with ether. The filtrate was extracted with ether, and the combined extracts evaporated to dryness. The residual oil was chromatographed on a 1/2 × 4 inch dry quartz column of silica gel. Elution with methylene chloride removed a first band of impurity, while further elution with ethylacetate produced the product. Evaporation of the eluate to dryness yielded 0.5 g (62% yield) of 4-ethynyl-o-phenylenediamine.
Workup
- additionwas added a solution
- filtrationwas filtered by suction
- washthe residue was washed with ether
- extractionThe filtrate was extracted with ether
- customthe combined extracts evaporated to dryness
- customThe residual oil was chromatographed on a 1/2 × 4 inch dry quartz column of silica gel
- washElution with methylene chloride
- customremoved a first band of impurity
- washwhile further elution with ethylacetate
- customproduced the product
- customEvaporation of the eluate to dryness
Sources & evidence
- ORD record
- ord-29970ac1dced45ad9e7fa3de7edf5be5
- Source dataset
- uspto-grants-1977_01
- Patent number
- US04005144
Reaction notes
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