Diethyl Oxalate → HCID 178517317, compound

HRID 1731924Notes

Reaction equation

HRID 1731924 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11](OCC)(=[O:17])[C:12](OCC)=[O:13]>>[OH:13][C:12]1[C:11]([OH:17])=[N:10][C:4]2[C:5](=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)[N:9]=1

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 178517317HCID 178517317, compound

Procedure

A mixture consisting of 11.3 g. (0.0784 mole) of 4,5-difluoro-o-phenylenediamine (U.S. Pat. No. 4,264,600) and 80 ml. (0.589 mole) of diethyl oxalate was refluxed for a period of four hours to give a thick precipitate of product. The spent reaction mixture was then cooled to room temperature (~20° C.) overnight, filtered and the solid product so obtained was thereafter washed several times with diethyl ether and air-dried to constant weight to ultimately afford 15.5 g of pure 2,3-dihydroxy-6,7-difluoroquinoxaline, m.p. >310° C. Mass Spectrum: m/e, 198 (P+).

Workup

  1. customto give a thick precipitate of product
  2. customThe spent reaction mixture
  3. filtrationfiltered
  4. customthe solid product so obtained
  5. washwas thereafter washed several times with diethyl ether
  6. dry with materialair-dried to constant weight to ultimately afford 15.5 g of pure 2,3-dihydroxy-6,7-difluoroquinoxaline, m.p. >310° C

Sources & evidence

ORD record
ord-5adfd57b92d64b0b95a13026268d01eb
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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