Water → HCID 19365503, compound

HRID 849942Notes

Reaction equation

HRID 849942 reaction equation
O.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([N+:10]([O-])=O)=[CH:5][C:4]=1[C:13]1[C:14](=[O:24])[N:15]([CH3:23])[C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:18]=1>C(O)(=O)C.[Fe]>[NH2:10][C:6]1[C:7]([Cl:9])=[CH:8][C:3]([Cl:2])=[C:4]([C:13]2[C:14](=[O:24])[N:15]([CH3:23])[C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:18]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 962WaterHCID 19365489HCID 19365489, compound2×

Product 1

HCID 19365503HCID 19365503, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

Then, 0.59 g of iron powder was added to a mixture of 5.3 ml of acetic acid and 3.2 ml of water, to which a solution of 0.65 g of 3-(2,4-dichloro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-333) in 1.6 ml of acetic acid was slowly added dropwise, and the mixture was stirred at room temperature for 2 hours. 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 then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated, which afforded 0.49 g (yield, 82%) of 3-(5-amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-334; m.p., 188.7° C.).

Workup

  1. additionwas slowly added dropwise
  2. customAfter completion of the reaction
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated sodium hydrogencarbonate solution, water
  5. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5b1c397ffcc04efe9a040fc458236b61
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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