HCID 54336608, compound → HCID 20378935, compound

HRID 2052160Notes

Reaction equation

HRID 2052160 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH:7]=[C:8]([CH3:19])[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:10])([O-])=O.[H][H]>C(O)C.[C].[Pd]>[ClH:18].[CH3:19][CH:8]([CH2:7][C:6]1[CH:20]=[CH:21][CH:22]=[C:4]([NH2:1])[CH:5]=1)[C:9]([O:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)=[O:10]

Participants

5

Reactant 2

HCID 54336608HCID 54336608, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20378935HCID 20378935, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 250 ml of ethanol were suspended 28.5 g of the p-chlorophenyl m-nitro-α-methylcinnamate thus obtained and 3.0 g of 10% palladium-carbon, and gaseous hydrogen was introduced into the resulting suspension with stirring. About 8.5 liters of hydrogen was absorbed in 2 hours. After the reaction, the palladium catalyst was filtered off and the solvent was removed by distillation under reduced pressure. The residue was dissolved in 200 ml of ethyl ether, and gaseous hydrogen chloride was introduced into the resulting solution to obtain p-chlorophenyl α-methyl-β-(m-aminophenyl)-propionate hydrochloride in the form of colorless crystals. Yield: 23.0 g (78.5%); melting point: 85°-95° C.; IR (cm-1): 3500-2500, 1748, 1492.

Workup

  1. customthus obtained
  2. customAbout 8.5 liters of hydrogen was absorbed in 2 hours
  3. customAfter the reaction
  4. filtrationthe palladium catalyst was filtered off
  5. customthe solvent was removed by distillation under reduced pressure
  6. dissolutionThe residue was dissolved in 200 ml of ethyl ether
  7. additiongaseous hydrogen chloride was introduced into the resulting solution

Sources & evidence

ORD record
ord-d8b8c45c73c440768751f5b34d2be4f4
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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