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

HRID 1856544Notes

Reaction equation

HRID 1856544 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]>C(O)(C)C>[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 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Example 6 was repeated using 50 grams of 3-nitrophenylacetylene (19% wt. conc.) in isopropanol in the presence of 8.0 grams of said cobalt polysulfide catalyst (weight ratio of NPA to Co of 50:1) for 1.1 hours at 120° C. and 1000 psig (6.9 MPa) of hydrogen pressure. Analysis showed quantitative conversion and 82% yield of 3-aminophenylacetylene. All byproducts were polymeric. The results are summarized in Table 1 below.

Workup

  1. customfor 1.1 hours
  2. customat 120° C.

Sources & evidence

ORD record
ord-5cd7b47d977946e6b0a8320bd0459c99
Source dataset
uspto-grants-1980_08
Patent number
US04219679

Reaction notes

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