3-(2-Fluoro-4-methoxycarbonylmethoxy-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1h)-pyridone → 3-(7-fluoro-2,3-dihydro-1,4-benzoxazin-3-on-6-yl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone

HRID 1385931Notes

Reaction equation

HRID 1385931 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([O:12]C)=O)[C:5]([N+:14]([O-])=O)=[CH:4][C:3]=1[C:17]1[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=1>C(O)(=O)C.[Fe]>[F:1][C:2]1[C:3]([C:17]2[C:18](=[O:28])[N:19]([CH3:27])[C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=2)=[CH:4][C:5]2[NH:14][C:10](=[O:12])[CH2:9][O:8][C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 154570543-(2-Fluoro-4-methoxycarbonylmethoxy-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1h)-pyridone

Product 1

HCID 184083243-(7-fluoro-2,3-dihydro-1,4-benzoxazin-3-on-6-yl)-1-methyl-6-trifluoromethyl-2(1H)-pyridoneYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

1.5 g (3.7 mmol) of 3-(2-fluoro-4-methoxycarbonylmethoxy-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 50 ml of acetic acid, and 0.64 g (11.5 mmol) of iron powder was added under heating and refluxing, followed by stirring for 1 hour. The reaction solution was subjected to filtration, and the filtrate was distilled off under reduced pressure. The obtained residue was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and then, the obtained residue was purified by silica gel column chromatography to obtain 0.95 g (yield: 80%) of the desired product. Melting point: 216-218° C. 1H-NMR (400 MHz, CDCl3) δ value: 3.69(3H,s), 4.60(2H,s), 6.78(1H,d), 6.80(1H,d), 7.18(1H,d), 7.53(1H,d), 8.47(1H,s)ppm.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. filtrationThe reaction solution was subjected to filtration
  4. distillationthe filtrate was distilled off under reduced pressure
  5. additionThe obtained residue was poured into water
  6. extractionextracted with ethyl acetate
  7. washAfter washing with water
  8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  9. distillationEthyl acetate was distilled off under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ab0355fb69504f3288c8b05c9b59ea1d
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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