1,3-Diethyl 2-oxopropanedioate → HCID 6320214, compound

HRID 1414081Notes

Reaction equation

HRID 1414081 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[H][H].[C:15](OCC)(=[O:23])[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=O>[Pd].C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:7][C:8]=1[F:9])[N:6]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:15](=[O:23])[NH:10]2

Participants

6

Reactant 3

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 1571514,5-Difluoro-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 6320214HCID 6320214, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A reaction mixture was prepared containing 8.75 g. of 4,5-difluoro-2-nitroaniline, 200 ml. of ethanol, and as a catalyst 1 g. of 10 percent palladium-on-carbon. The mixture was hydrogenated until the theoretical amount of hydrogen had been absorbed, using a low-pressure hydrogenation apparatus. The catalyst was separated by filtration using standard precautions and the product of the reaction, 4,5-difluoro-o-phenylenediamine, was reacted with diethyl mesoxalate following the procedure of Preparation 1 without further purification. The product of this reaction, ethyl 6,7-difluoro-3,4-dihydro-3-keto-2-quinoxaline carboxylate, melted at about 193°-195° C.

Workup

  1. customA reaction mixture was prepared
  2. additioncontaining 8.75 g
  3. customhad been absorbed
  4. customThe catalyst was separated by filtration
  5. customthe product of the reaction, 4,5-difluoro-o-phenylenediamine
  6. customthe procedure of Preparation 1
  7. customwithout further purification
  8. customThe product of this reaction, ethyl 6,7-difluoro-3,4-dihydro-3-keto-2-quinoxaline carboxylate, melted at about 193°-195° C.

Sources & evidence

ORD record
ord-b581cc22af314b0eadd702cd5db8286b
Source dataset
uspto-grants-1981_02
Patent number
US04252954

Reaction notes

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