Methane → Methyl 3-aminocinnamate

HRID 1414801Notes

Reaction equation

HRID 1414801 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1.C.[H][H]>CO.[Pt]=S>[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 1018253-(3-Nitrophenyl)acrylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 54385173Methyl 3-aminocinnamateYield 100.6%

Reagents, catalysts & solvents 2

HCID 82861Platinum sulfide (PtS)CatalystHCID 887MethanolSolvent

Procedure

50 g of 3-nitrocinnamic acid methyl ester in 350 ml of methanol are hydrogenated in the presence of 1.5 g of the platinum sulphide catalyst described in Example 6 (5% strength on active charcoal) for 2 hours at 70° C and one half hour at 80° C under 130 bars hydrogen pressure in a stirred autoclave of 700 ml capacity. The pressure drop has ceased after 2 hours. The solution is freed from the catalyst and evaporated. 43 g of crystalline 3-aminocinnamic acid methyl ester of melting point 75° C are obtained.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-af5f12a7792b46798d03e7e509001278
Source dataset
uspto-grants-1977_01
Patent number
US04002673

Reaction notes

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