1-(3-Chloro-2-fluoro-6-nitrophenoxy)-2-propanone → HCID 13188587, compound

HRID 851084Notes

Reaction equation

HRID 851084 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([Cl:13])[CH:9]=[CH:8][C:7]=1[N+:14]([O-])=O)[C:2]([CH3:4])=O>C(O)C.[Ni]>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]2[NH:14][CH:2]([CH3:4])[CH2:1][O:5][C:6]=2[C:11]=1[F:12]

Participants

4

Reactant 1

HCID 131885861-(3-Chloro-2-fluoro-6-nitrophenoxy)-2-propanone

Product 1

HCID 13188587HCID 13188587, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

2.3 g (7.9 mmols) of 2-acetonyloxy-4-chloro-3-fluoronitrobenzene was dissolved in 30 ml of ethanol and catalytically reduced in the presence of 2 g of Raney nickel. After completion of the reduction, the catalyst was removed by filtration, and the filtrate was concentrated. The resulting residue was purified by silica gel (20 g) column chromatography using chloroform as an eluant to provide 1.2 g (75.5% yield) of 7-chloro-8-fluoro-3-methyl-2,3-dihydro-4H-1,4-benzoxazine as an oil.

Workup

  1. customAfter completion of the reduction, the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by silica gel (20 g) column chromatography

Sources & evidence

ORD record
ord-d37ce0e08bc44a22b7e9c6d5df77b00e
Source dataset
uspto-grants-1983_05
Patent number
US04382892

Reaction notes

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