HCID 3119475, compound → HCID 53885574, compound

HRID 342242Notes

Reaction equation

HRID 342242 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])([O-])=O.[H][H]>C(C(C)=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8]

Participants

4

Reactant 2

HCID 3119475HCID 3119475, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53885574HCID 53885574, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a stirred autoclave, 0.5 g of a catalyst prepared according to Example H1 and containing 0.182 g of Pb(OAc)2 3H2O (corresponding to 2% Pb), and 50 mg (0.5mol %) of FeCl2 4H2O are added to a solution of 10.4 g of propargyl 3-nitrobenzoate in 100 ml of methyl ethyl ketone. The mixture is then hydrogenated for 14 hours at a temperature of 140° C. and at a hydrogen pressure of 20 bar. The catalyst is filtered off, the solvent is distilled off and the remaining mixture is purified by column chromatography to give 5.8 g of propargyl 3-aminobenzoate. The content of allyl 3-aminobenzoate according to 1H--NMR is 18%.

Workup

  1. filtrationThe catalyst is filtered off
  2. distillationthe solvent is distilled off
  3. customthe remaining mixture is purified by column chromatography

Sources & evidence

ORD record
ord-4211480b8b8442dc859c837151d70b76
Source dataset
uspto-grants-1999_01
Patent number
US05856578

Reaction notes

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