HCID 20406198, compound → HCID 13394303, compound

HRID 2164307Notes

Reaction equation

HRID 2164307 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:6][C:5]([CH3:17])=[CH:4][C:3]=1[CH:18](SCCC)[C:19]([NH2:21])=[O:20]>O1CCCC1.[Ni]>[NH2:1][C:2]1[C:7]([C:8](=[O:16])[C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)=[CH:6][C:5]([CH3:17])=[CH:4][C:3]=1[CH2:18][C:19]([NH2:21])=[O:20]

Participants

4

Reactant 1

HCID 20406198HCID 20406198, compound

Product 1

HCID 13394303HCID 13394303, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 60.0 (0.167 mole) of 2-amino-3-(4-fluorobenzoyl)-5-methyl-α-(propylthio)phenylacetamide in 2.4 liters of tetrahydrofuran was treated with 400 g of wet Raney nickel (washed with water and titrated to constant pH 7 with acetic acid, washed again with water and then washed 3 times with tetrahydrofuran). The mixture was filtered and the filtrate was concentrated. The residue was triturated with hot isopropyl ether and recrystallized from isopropyl alcohol to give 43.6 (91%) of the titled compound as bright yellow crystals, m.p. 203°-206° C.

Workup

  1. washwashed with water
  2. washwashed again with water
  3. washwashed 3 times with tetrahydrofuran)
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with hot isopropyl ether
  7. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-40bc7290abc64d968b88995543412957
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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