Ammonia → HCID 53754019, compound

HRID 323207Notes

Reaction equation

HRID 323207 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
50 °C

Procedure

Combine 3-cyano-3-phenylpentanedioic acid diethyl ester (243 g, 0.84 mol) and ethanol (2.5 L), concentrated aqueous ammonia (325 mL), and Raney nickel (250 g, prewashed three times with water) in a two gallon autoclave. Charge with 200 psi of hydrogen. Heat to 50° C. After 24 hours, vent the reactor and purge with nitrogen. Filter the reaction mixture through a celite pad and rinse the solids with ethanol (1 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 L)
  4. customEvaporate the filtrate in vacuo

Sources & evidence

ORD record
ord-53fbfe43c37f407488c2e02cc8073138
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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