Ammonia → HCID 53754019, compound

HRID 323206Notes

Reaction equation

HRID 323206 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]([C:19]#[N:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][C:8](OCC)=[O:9])[CH3:2].N.[H][H]>[Ni].C(O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C:8](=[O:9])[NH:20][CH2:19]1)[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 54389077HCID 54389077, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53754019HCID 53754019, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
24 °C

Procedure

Combine 3-cyano-3-phenylpentanedioic acid diethyl ester (396.6 g, 1.37 mol) and ethanol (4 L), and concentrated aqueous ammonia (530 mL), in a two gallon autoclave. Add Raney nickel (410 g). Heat to 24° C. and charge with 205 psi of hydrogen. After 26 hours, vent the reactor and purge with nitrogen. Filter the reaction mixture through a celite pad and rinse the solids with ethanol (1.5 L). Evaporate the filtrate in vacuo to give the title compound.

Workup

  1. custompurge with nitrogen
  2. filtrationFilter the reaction mixture through a celite pad
  3. washrinse the solids with ethanol (1.5 L)
  4. customEvaporate the filtrate in vacuo

Sources & evidence

ORD record
ord-103b0ed8142a41cb8e52a92aa86a8410
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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