Ammonia → HCID 16776951, compound

HRID 911286Notes

Reaction equation

HRID 911286 reaction equation
[C:1]([NH:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].N>CO.[Ni]>[NH2:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([NH:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 15295328HCID 15295328, compound

Product 1

HCID 16776951HCID 16776951, compoundYield 108.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Combine N-tert-butyl-4-cyano-benzamide (0.4 g, 1.78 mmol), Raney® 3201 nickel (slurry in water, 0.03 g), 2N ammonia in methanol (20 mL) and hydrogenate at 50 psi for 1 h. Filter the reaction mixture through a pad of Celite®, remove the solvent and purify by SCX chromatography to obtain the title compound as a colorless oil (0.4 g, 95%). MS (ES+) m/z: 207 (M+H)+.

Workup

  1. filtrationFilter the reaction mixture through a pad of Celite®
  2. customremove the solvent
  3. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-be1a6da09ff1430194951b782ca5380f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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