HCID 14276966, compound → HCID 14276967, compound

HRID 1164730Notes

Reaction equation

HRID 1164730 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:16](=[O:17])[N:15]([CH3:18])[C:14](=[O:19])[CH:13]=[N:12]2)=[C:4]([F:20])[CH:3]=1>C(O)C.[Pt]=O>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:20])=[C:5]([N:11]2[C:16](=[O:17])[N:15]([CH3:18])[C:14](=[O:19])[CH:13]=[N:12]2)[CH:6]=1

Participants

4

Reactant 1

HCID 14276966HCID 14276966, compound

Product 1

HCID 14276967HCID 14276967, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 18.0 g (0.060 mole) of 2-(4-chloro-2-fluoro-5-nitrophenyl)-4-methyl-1,2,4-triazine-3,5-(2H,4H)dione in 200 mL of ethanol was placed in a 500 mL Parr hydrogenation bottle with 0.5 g of platinum oxide. The bottle was placed in a Parr hydrogenator and the reaction mixture hydrogenated. Upon complete hydrogenation the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under reduced pressure to a residual oil. The oil was purified using column chromatography on silica gel. Elution was accomplished with 1:1--ethyl acetate: heptane. The appropriate fractions were combined and concentrated under reduced pressure to yield 13.0 g of 2-(5-amino-4-chloro-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione; m.p. 150-152° C.

Workup

  1. filtrationUpon complete hydrogenation the reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  4. customThe oil was purified
  5. washElution
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-567b485d590c43038123e88730ee48c0
Source dataset
uspto-grants-1990_03
Patent number
US04906287

Reaction notes

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