HCID 22267250, compound → HCID 22267242, compound

HRID 488883Notes

Reaction equation

HRID 488883 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-])=O)[CH:29]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:37]>C(O)C.C1COCC1.[Ni]>[NH2:34][C:30]1[CH:29]=[C:28]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([CH3:37])[CH:4]=3)[O:9][C:8](=[O:12])[C:7]=2[CH2:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[C:24]([F:26])([F:27])[F:25])=[O:15])[CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 1

HCID 22267250HCID 22267250, compound

Product 1

HCID 22267242HCID 22267242, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture solution of 2-[7-chloro-6-methyl-4-(3-nitrophenyl)-2-oxo-2H-chromen-3-yl]-N-[4-chloro-2-(trifluoromethyl)phenyl]acetamide (300 mg) in ethanol (2 ml) and THF (5 ml) was combined with Raney-nickel (50 mg), and stirred under hydrogen atmosphere at room temperature for 5 hours. After catalyst was filtered off, the reaction solution was concentrated. The resultant residue was purified by a silica gel chromatography (eluent: hexane-ethyl acetate=2:1), and further recrystallized from THF-ethyl acetate to obtain the title compound as a colorless crystal (166 mg, yield: 59%). Melting point: 206-207° C.

Workup

  1. filtrationAfter catalyst was filtered off
  2. concentrationthe reaction solution was concentrated
  3. customThe resultant residue was purified by a silica gel chromatography (eluent: hexane-ethyl acetate=2:1)
  4. customfurther recrystallized from THF-ethyl acetate

Sources & evidence

ORD record
ord-bbdf17d30d0349d5afb09024a2c22d66
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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