HCID 22921473, compound → HCID 22921474, compound

HRID 2258417Notes

Reaction equation

HRID 2258417 reaction equation
[C:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)([CH2:10][CH3:11])[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:2]>O=[Pt]=O.C(O)C>[C:1]([C:3]([C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)([CH2:10][CH3:11])[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

4

Reactant 1

HCID 22921473HCID 22921473, compound

Product 1

HCID 22921474HCID 22921474, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A 3-necked round-bottomed flask was charged with methyl 4-cyano-4-(4-nitrophenyl)hexanoate (20.0 g), 90% ethanol (1000 ml) and PtO2 (1.0 g). The vessel was then evacuated and charged with nitrogen. The mixture was stirred vigorously and subjected to H2 at atmospheric pressure supplied via a balloon. The catalyst was removed by filtration through celite and the solvent removed under reduced pressure to give methyl 4-cyano-4-(4-aminophenyl)-hexanoate (18 g, 100%) as a viscous, brown oil.

Workup

  1. customThe vessel was then evacuated
  2. additioncharged with nitrogen
  3. customThe catalyst was removed by filtration through celite
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-46dd9db255084e1496c20b53acff6c72
Source dataset
uspto-grants-1997_08
Patent number
US05661014

Reaction notes

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