Ethyl 3-(3-chlorophenyl)-4-nitrobutanoate → Ethyl 4-amino-3-(3-chlorophenyl)butanoate

HRID 1663561Notes

Reaction equation

HRID 1663561 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:15][N+:16]([O-])=O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1>C(O)C.[Ni]>[NH2:16][CH2:15][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 1

HCID 22387109Ethyl 3-(3-chlorophenyl)-4-nitrobutanoate

Product 1

HCID 22387061Ethyl 4-amino-3-(3-chlorophenyl)butanoateYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

In a 2 L pressure jar, under inert atmosphere, 196 g (733 mmoles) of ethyl 3-(3-chlorophenyl)-4-nitrobutanoate 377 are dissolved in 200 ml of ethanol. A suspension of 200 g of predried (3×, ethanol) Raney Nickel in 700 ml of ethanol is added and the mixture hydrogenated on a Parr hydrogenator at a maximum of 20 psi H2 pressure (STRONGLY EXOTHERMIC REACTION, ice/water cooling required). The mixture is degassed, filtered on a Celite/Norite pad, and the filtrate concentrated in vacuo, to give 136.7 g of crude 378, 78% yield, used as such in the next step.

Workup

  1. additionis added
  2. customThe mixture is degassed
  3. filtrationfiltered on a Celite/Norite pad
  4. concentrationthe filtrate concentrated in vacuo
  5. customto give 136.7 g of crude 378, 78% yield

Sources & evidence

ORD record
ord-53f6261992144e0dbc231eff4ecc1006
Source dataset
uspto-grants-2011_10
Patent number
US08034958B2

Reaction notes

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