2-Amino-3-benzoyl-alpha-(methylthio)benzeneacetonitrile → 2-Amino-3-benzoylbenzeneacetonitrile

HRID 1199012Notes

Reaction equation

HRID 1199012 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH:16](SC)[C:17]#[N:18]>O1CCCC1.[Ni]>[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]#[N:18]

Participants

4

Reactant 1

HCID 156347292-Amino-3-benzoyl-alpha-(methylthio)benzeneacetonitrile

Product 1

HCID 156347312-Amino-3-benzoylbenzeneacetonitrileYield 72%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 19.4 g (0.069 mole) of 2-amino-3-benzoyl-α-(methylthio)benzeneacetonitrile in 200 ml of tetrahydrofuran was added 160 g of commercial Raney nickel which had been washed three times with water and three times with tetrahydrofuran. The mixture was stirred at ambient temperature for 10 minutes and then filtered. The filtrate obtained was concentrated to give a solid residue. This residue was recrystallized from 2-propanol to yield 11.7 g (72%) of the titled compound as bronze needles, m.p. 137.5°-139° C.

Workup

  1. washhad been washed three times with water and three times with tetrahydrofuran
  2. filtrationfiltered
  3. customThe filtrate obtained
  4. concentrationwas concentrated
  5. customto give a solid residue
  6. customThis residue was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-7b7d46b850104894a9c2fa144d565eb4
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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