Water → HCID 19365532, compound

HRID 849935Notes

Reaction equation

HRID 849935 reaction equation
O.[Cl:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:17]=2)=[C:5]([F:24])[CH:4]=1>C(O)(=O)C.[Fe]>[NH2:9][C:8]1[C:3]([Cl:2])=[CH:4][C:5]([F:24])=[C:6]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:17]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 962Water2×HCID 19365540HCID 19365540, compound2×

Product 1

HCID 19365532HCID 19365532, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

Then, 0.37 g of iron powder was added to a mixture of 5.3 ml of acetic acid and 2.0 ml of water, to which a solution of 0.39 g of 3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-17) in 1.0 ml of acetic acid was slowly added dropwise, and the mixture was stirred at room temperature for 3.5 hours. After completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed twice with water and further with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated, which afforded 0.16 g (yield, 46%) of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-23).

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 twice with water and further with saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-52eade3fa3c248bc8d8b9c9721da0a4b
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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