1-Methylcyclohexyl 2-(p-nitrophenyl)propionate → 1-Methylcyclohexyl 2-(p-aminophenyl)-propionate

HRID 34538

Reaction equation

HRID 34538 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:21])[C:11]([O:13][C:14]2([CH3:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:21])[C:11]([O:13][C:14]2([CH3:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 540684921-Methylcyclohexyl 2-(p-nitrophenyl)propionateHCID 178418361HCID 178418361, compound

Product 1

HCID 137540711-Methylcyclohexyl 2-(p-aminophenyl)-propionateYield 67.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of 34.9 g of 1-methylcyclohexyl 2-(p-nitrophenyl)-propionate in 250 ml of absolute ethanol was hydrogenated at atmospheric pressure in the presence of 10% palladium on carbon catalyst. After the uptake of hydrogen gas was complete, the catalyst was filtered off through celite and the filtrate was evaporated to dryness. Trituration of the residue with petroleum ether gave 21.02 g (67% yield) of 1-methylcyclohexyl 2-(p-aminophenyl)-propionate as creamy white crystals melting at 85°-87° C.

Workup

  1. filtrationthe catalyst was filtered off through celite
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-15fc9e5b04644708b922aada49328d83
Source dataset
uspto-grants-1988_08
Patent number
US04762840

Linked notes

Loading…