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

HRID 323196Notes

Reaction equation

HRID 323196 reaction equation
N.[CH2:2]([O:4][C:5](=[O:24])[CH2:6][C:7]([C:22]#[N:23])([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[CH2:8][C:9](OCC)=[O:10])[CH3:3]>[Ni].C(O)C>[CH2:2]([O:4][C:5](=[O:24])[CH2:6][C:7]1([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:8][C:9](=[O:10])[NH:23][CH2:22]1)[CH3:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 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 702EthanolSolvent

Procedure

Combine Raney nickel (24 lb) and an aqueous concentrated ammonia solution (19 lb). Add a solution of 3-cyano-3-(3,4-dichlorophenyl)pentanedioic acid diethyl ester (15 lb) and ethanol (117 lb) in a pressure reactor. Hydrogenate at 200 psi and 35° C. After 20 hours, cool, vent the vessel, purge with nitrogen, and filter. Rinse the solids with ethanol. Evaporate the filtrate in vacuo to give a residue. Crystallize the residue by dissolving in ethyl acetate and triturate the solution with heptane to give a solid. Collect the solid to give the title compound. Elemental Analysis calculated for C14H15Cl2NO3: C 53.18; H 4.78; N 4.43; Found: C 53.18; H 4.72; N 4.46.

Workup

  1. customat 200 psi and 35° C
  2. temperaturecool
  3. custompurge with nitrogen
  4. filtrationfilter
  5. washRinse the solids with ethanol
  6. customEvaporate the filtrate in vacuo
  7. customto give a residue
  8. customCrystallize the residue
  9. dissolutionby dissolving in ethyl acetate
  10. customtriturate the solution with heptane
  11. customto give a solid
  12. customCollect the solid

Sources & evidence

ORD record
ord-c7cb413e8b6b441d844b8f1a19adf5ea
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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