Ammonia → HCID 21867934, compound

HRID 895321Notes

Reaction equation

HRID 895321 reaction equation
[NH:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:20])[CH2:16][C:17](=O)[CH3:18])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:21].[H][H]>C1(C)C=CC=CC=1.[Ni]>[NH2:21][CH:17]([CH3:18])[CH2:16][C:15]([NH:14][C:11]1[CH:12]=[CH:13][C:8]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1)=[O:20]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 879512HCID 879512, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21867934HCID 21867934, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1140TolueneSolvent

Procedure

Thirty grams (0.11 mol) of N-(4-anilinophenyl)-3-oxo butanamide was dissolved in 300 ml of toluene. This was mixed with 30 g. (1.8 mol) of anhydrous ammonia, Raney nickel catalyst, and 800 psi of hydrogen gas at a temperature of 70° C. for 2 hours. The catalyst was removed and the solvent stripped off under vacuum. Purification was done by flash chromatography and recrystallization from hot toluene. The product was obtained in a yield of 16 g. with a melting point of 130-132° C.

Workup

  1. additionThis was mixed with 30 g
  2. customThe catalyst was removed
  3. customPurification
  4. customwas done by flash chromatography and recrystallization from hot toluene
  5. customThe product was obtained in a yield of 16 g

Sources & evidence

ORD record
ord-8a90bf05963a494aa5d99e3857fcaa01
Source dataset
uspto-grants-2005_07
Patent number
US06916767B2

Reaction notes

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