4-Ethynyl-1,2-dinitrobenzene → 1,2-Benzenediamine, 4-ethynyl- (9CI)

HRID 1283514Notes

Reaction equation

HRID 1283514 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

5

Reactant 1

HCID 214824734-Ethynyl-1,2-dinitrobenzene

Product 1

HCID 214824711,2-Benzenediamine, 4-ethynyl- (9CI)Yield 62%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolvent

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. Evaportion of the eluate to dryness yielded 0.5 g (62% yield) of 4-ethynyl-o-phenylenediamine.

Workup

  1. additionwas added a solution
  2. filtrationwas filtered by suction
  3. washthe residue was washed with ether
  4. extractionThe filtrate was extracted with ether
  5. customthe combined extracts evaporated to dryness
  6. customThe residual oil was chromatographed on a 1/2 × 4 inch dry quartz column of silica gel
  7. washElution with methylene chloride
  8. customremoved a first band of impurity
  9. washwhile further elution with ethylacetate
  10. customproduced the product

Sources & evidence

ORD record
ord-68d42ac254fb402abe58b811e95aff94
Source dataset
uspto-grants-1976_08
Patent number
US03975444

Reaction notes

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