HCID 13772846, compound → HCID 13853639, compound

HRID 868100Notes

Reaction equation

HRID 868100 reaction equation
[C:1]([C:4]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([N+:16]([O-])=O)[C:5]=1[O:6][CH2:7][C:8](=O)[CH3:9])(=[O:3])[CH3:2].[H][H]>[Ni].C(O)C>[F:15][C:14]1[CH:13]=[CH:12][C:11]2[NH:16][CH:8]([CH3:9])[CH2:7][O:6][C:5]=2[C:4]=1[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 13772846HCID 13772846, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13853639HCID 13853639, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.98 g (19.5 mmole) of 1-(2-acetyl-3-fluoro-6-nitrophenoxy)-2-propanone, 100 ml of 95% ethanol and 1 g of Raney nickel was shaken in an atmosphere of hydrogen at 4.5×105Pa at room temperature for 18 hours. The reaction was filtered and the solvent removed at reduced pressure. The residue was chromatographed on silica, with hexane:ether (1:1) to give 2.76 g of 1-(7-fluoro-3,4-dihydro-3-methyl-2H-1,4-benzoxazin-8-yl)ethanone.

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent removed at reduced pressure
  3. customThe residue was chromatographed on silica, with hexane:ether (1:1)

Sources & evidence

ORD record
ord-7287dcdea0ff45bca7415ca2e17284a5
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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