Acetic Acid → HCID 19365539, compound

HRID 849931Notes

Reaction equation

HRID 849931 reaction equation
C(O[C:6]([CH2:8][O:9][C:10]1[C:15]([N+:16]([O-])=O)=[CH:14][C:13]([C:19]2[C:20](=[O:30])[N:21]([CH3:29])[C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][N:24]=2)=[CH:12][CH:11]=1)=[O:7])CCC.[H][H].C(O)(=O)C.O>C(OCC)(=O)C.[Pd]>[O:7]=[C:6]1[NH:16][C:15]2[CH:14]=[C:13]([C:19]3[C:20](=[O:30])[N:21]([CH3:29])[C:22]([C:25]([F:26])([F:27])[F:28])=[CH:23][N:24]=3)[CH:12]=[CH:11][C:10]=2[O:9][CH2:8]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 19365501HCID 19365501, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19365539HCID 19365539, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Then, 0.24 g of 10% palladium/carbon was added to a solution of 1.25 g of 3-[4-(butoxycarbonylmethoxy)-5-nitrophenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine in 36 ml of ethyl acetate under an atmosphere of nitrogen, which was then replaced with hydrogen under a pressure of 1 atm., and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was filtered through celite and concentrated. To the crude product obtained was added 2.0 ml of acetic acid, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium hydrogencarbonate solution, water, and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 0.45 g (yield, 48%) of 3-(3-oxo-2H-1,4-benzoxazin-6-yl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 2-1; m.p., 191.1° C.).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite and
  3. concentrationconcentrated
  4. customTo the crude product obtained
  5. stirringthe mixture was stirred at room temperature for 1 hour
  6. customAfter completion of the reaction
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with saturated sodium hydrogencarbonate solution, water
  9. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c9b40cd9aca346819e4fe1fe6f3800ee
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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