2-Amino-3-(4-chlorobenzoyl)-alpha-(methylthio)benzeneacetonitrile → 2-Amino-3-(4-chlorobenzoyl)benzeneacetonitrile

HRID 1199013Notes

Reaction equation

HRID 1199013 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH:17](SC)[C:18]#[N:19]>[Ni].O1CCCC1>[NH2:1][C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:17][C:18]#[N:19]

Participants

4

Reactant 1

HCID 156347302-Amino-3-(4-chlorobenzoyl)-alpha-(methylthio)benzeneacetonitrile

Product 1

HCID 156347322-Amino-3-(4-chlorobenzoyl)benzeneacetonitrileYield 56%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 280 g sample of a commercial Raney nickel preparation was washed twice with water, titrated to a pH of 7 with acetic acid, washed twice with water and three times with tetrahydrofuran. The Raney nickel preparation was then slurried in 300 ml of tetrahydrofuran and added to a stirred solution of 34.4 g (0.11 mole) of 2-amino-3-(4-chlorobenzoyl)-α-(methylthio)benzeneacetonitrile in 250 ml of tetrahydrofuran. The resulting mixture was stirred at ambient temperature for 10 minutes, filtered through Celite, and the filtrate concentrated to give a solid as a residue. This solid residue was recrystallized from acetonitrile to yield 16.4 g (56%) of the titled compound as brown crystals, m.p. 181°-2° C.

Workup

  1. washwas washed twice with water
  2. washwashed twice with water and three times with tetrahydrofuran
  3. customThe Raney nickel preparation
  4. filtrationfiltered through Celite
  5. concentrationthe filtrate concentrated
  6. customto give a solid as a residue
  7. customThis solid residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-511a71410e5641a7983a213abf266a31
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

Loading…