Ammonia → 3-(4-(Trifluoromethyl)phenyl)pyrrolidin-2-one

HRID 1667292Notes

Reaction equation

HRID 1667292 reaction equation
[C:1]([CH2:3][CH:4]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[C:5](OCC)=[O:6])#[N:2].N>CO.[Ni].O>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([CH:4]2[CH2:3][CH2:1][NH:2][C:5]2=[O:6])=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 67360010Ethyl 3-cyano-2-(4-(trifluoromethyl)phenyl)propanoate

Product 1

HCID 673587773-(4-(Trifluoromethyl)phenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 935NickelSolventHCID 962WaterSolvent

Procedure

A solution of the product from Example 266B (4.1 g, 15.12 mmol) in methanol (10 mL) was added to 7 M ammonia in methanol (5.00 mL) and Raney® nickel, water wet, A-7000 (12.30 g, 210 mmol) in a 250 mL stainless steel pressure bottle and stirred for 16 hours under hydrogen (30 psi) at room temperature. The mixture was filtered through a nylon membrane and then concentrated to obtain solid. The solid was slurried in 5% ethyl acetate/hexanes, filtered and dried to give the title compound. MS (DCI+) m/z 247 (M+NH4)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated
  3. customto obtain solid
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-dc55c4631c6d4b8e9bc53f41879a215a
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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