Ammonia → HCID 57656128, compound

HRID 911290Notes

Reaction equation

HRID 911290 reaction equation
[C:1]([NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:8]=1[F:15])([CH3:4])([CH3:3])[CH3:2].N>CO.[Ni]>[NH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:16])=[C:8]([F:15])[CH:9]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 2989257HCID 2989257, compound

Product 1

HCID 57656128HCID 57656128, compoundYield 150.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Combine N-tert-butyl-4-cyano-2-fluoro-benzamide (0.6 g, 1.78 mmol), Raney® 3201 nickel (slurry in water, 30 mg), 2N ammonia in methanol (30 mL) and hydrogenate at 50 psi for 1 h. Filter the reaction mixture through a pad of Celite®, concentrate in vacuo and purify by SCX chromatography to obtain the title compound as a colorless oil (0.6 g, 96%).

Workup

  1. filtrationFilter the reaction mixture through a pad of Celite®
  2. concentrationconcentrate in vacuo
  3. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-e60894abacac4792a4a0303e6b2fca10
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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