Ammonia → (3-(3,4-Dichlorophenyl)-5-oxopyrrolidin-3-yl)acetic acid ethyl ester

HRID 323197Notes

Reaction equation

HRID 323197 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]([C:21]#[N:22])([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)[CH2:7][C:8](OCC)=[O:9])[CH3:2].C(O)C.N>[Ni].O>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:7][C:8](=[O:9])[NH:22][CH2:21]1)[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 702EthanolHCID 54083037Diethyl 3-cyano-3-(3,4-dichlorophenyl)pentanedioate

Product 1

HCID 54080079(3-(3,4-Dichlorophenyl)-5-oxopyrrolidin-3-yl)acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

Combine 3-cyano-3-(3,4-dichlorophenyl)pentanedioic acid diethyl ester (6.7 kg, wet cake containing isopropanol, about 3% L.O.D.) and 3C ethanol (52 kg) in a pressure reactor. Add Raney nickel in water (17.5 kg, about 11 kg of active catalyst) and an aqueous concentrated ammonia solution (8.7 kg). Hydrogenate at 200 psi and 35° C. When the reaction is complete, cool, vent the reactor, and purge with nitrogen. Filter through a filter bag, rinse with ethanol, and then filter through a 0.2 micron cartridge filter, and rinse the solids with ethanol. Evaporate the filtrate in vacuo to give the title compound.

Workup

  1. customat 200 psi and 35° C
  2. temperaturecool
  3. custompurge with nitrogen
  4. filtrationFilter through a filter bag
  5. washrinse with ethanol
  6. filtrationfilter through a 0.2 micron cartridge
  7. filtrationfilter
  8. washrinse the solids with ethanol
  9. customEvaporate the filtrate in vacuo

Sources & evidence

ORD record
ord-eaefb956746f4671ae6d6c9effb56357
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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