Hydrochloric Acid → HCID 178501850, compound

HRID 2412929Notes

Reaction equation

HRID 2412929 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[C:6]([CH2:8][C:9](=[O:14])[C:10]([O:12][CH3:13])=[O:11])=[O:7].Cl.[N:21]([O-])=[O:22].[Na+]>CO>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([C:6](=[O:7])[C:8](=[N:21][OH:22])[C:9](=[O:14])[C:10]([O:12][CH3:13])=[O:11])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20431374HCID 20431374, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178501850HCID 178501850, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution was prepared by dissolving 40 g. of methyl 3-trifluoromethylbenzoylpyruvate in 300 ml. of methanol. N2O3Gas was slowly passed into the solution over a period of four hours (until all of the ester had dissolved plus one additional hour). N2O3 gas was generated by the dropwise addition of 12N aqueous hydrochloric acid into an aqueous slurry of sodium nitrite. Next, the solvent was removed from the reaction mixture and 200 ml. of water added to the residue. The aqueous mixture was extracted with three 300 ml. portions of ether. The ether extracts were separated, combined and the combined extracts dried. The ether was removed in vacuo leaving as a residue methyl 4-(3-trifluoromethylphenyl)-2,4-dioxo-3-oximinobutanoate formed in the above reaction.

Workup

  1. customA solution was prepared
  2. dissolutionby dissolving 40 g
  3. customNext, the solvent was removed from the reaction mixture and 200 ml
  4. additionof water added to the residue
  5. extractionThe aqueous mixture was extracted with three 300 ml
  6. customThe ether extracts were separated
  7. customthe combined extracts dried
  8. customThe ether was removed in vacuo

Sources & evidence

ORD record
ord-873381b0f9514aba8869db8306d52250
Source dataset
uspto-grants-1985_01
Patent number
US04495195

Reaction notes

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