Benzene, 1-ethynyl-3-nitro- → Benzenamine, 3-ethynyl-

HRID 1856543Notes

Reaction equation

HRID 1856543 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]#[CH:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>CO>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]#[CH:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 76432Benzene, 1-ethynyl-3-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 104682Benzenamine, 3-ethynyl-Yield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Example 3 was repeated using 25 grams of 3-nitrophenylacetylene (10% wt. conc.) in methanol in the presence of 16.0 grams of a cobalt polysulfide catalyst prepared as per Example 1. The weight ratio of NPA to Co was 25:1. Reaction was carried out at 120° C., 1000 psig (6.9 MPa) of hydrogen pressure for 0.5 hours. Analysis showed quantitative conversion of feed and a 70% yield of 3-aminophenylacetylene. All byproducts were polymeric and easily separated. The results are summarized in Table 1 below.

Workup

  1. customReaction
  2. customwas carried out at 120° C.

Sources & evidence

ORD record
ord-545464c43c8341c3a9a0c146c314578e
Source dataset
uspto-grants-1980_08
Patent number
US04219679

Reaction notes

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