Water → 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine

HRID 849924Notes

Reaction equation

HRID 849924 reaction equation
O.C(O[C:7]([CH2:9][O:10][C:11]1[C:16]([N+:17]([O-])=O)=[CH:15][C:14]([C:20]2[C:21](=[O:31])[N:22]([CH3:30])[C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][N:25]=2)=[C:13]([F:32])[CH:12]=1)=[O:8])CCC>C(OCC)(=O)C.C(O)(=O)C.[Fe]>[F:32][C:13]1[C:14]([C:20]2[C:21](=[O:31])[N:22]([CH3:30])[C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][N:25]=2)=[CH:15][C:16]2[NH:17][C:7](=[O:8])[CH2:9][O:10][C:11]=2[CH:12]=1

Participants

6

Reactant 2

HCID 962WaterHCID 193654963-[4-(Butoxycarbonylmethoxy)-2-fluoro5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine2×

Product 1

HCID 117276093-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazineYield 56.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Then, 2.8 g of iron powder was added to a mixture of 5 ml of acetic acid and 50 ml of water, and the mixture was heated to 50° C. To this was slowly added dropwise a solution of 2.8 g of 3-[4-(butoxycarbonylmethoxy)-2-fluoro-5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (the present compound obtained in step (3) above) in 25 ml of ethyl acetate and 25 ml of acetic acid. The mixture was stirred at an internal temperature of 60° to 70° C. for 1 hour. After completion of the reaction, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated, which afforded 1.22 g of 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 2-49; m.p., 182.5° C.).

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-06109099fd874d3594e9fd00c801ff6d
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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