2-(2-Amino-3-benzoylphenyl)-2-(methylsulfanyl)acetamide → Nepafenac

HRID 1446827Notes

Reaction equation

HRID 1446827 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]([NH2:19])=[O: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]([NH2:19])=[O:18]

Participants

4

Reactant 1

HCID 156347272-(2-Amino-3-benzoylphenyl)-2-(methylsulfanyl)acetamide

Product 1

HCID 151075NepafenacYield 73.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To an agitated solution of 9.7 g (0.032 mole) of 2-amino-3-benzoyl-α-(methylthio)-phenylacetamide in 100 ml of tetrahydrofuran was added 80 g of wet Raney nickel (washed 3 times with water and 3 times with tetrahydrofuran). After 10 minutes the mixture was filtered to remove Raney nickel and the filtrate concentrated under vacuum. The residue was crystallized from isopropyl alcohol to give 6.0 g (73%) of yellow needles, m.p. 178.5°-180.0° C.

Workup

  1. filtrationAfter 10 minutes the mixture was filtered
  2. customto remove Raney nickel
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe residue was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-c56c8a33497240bf8015012682433431
Source dataset
uspto-grants-1982_02
Patent number
US04313949

Reaction notes

Loading…