Diethyl Oxalate → HCID 178517187, compound

HRID 1731921Notes

Reaction equation

HRID 1731921 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[C:10](OCC)(=[O:16])[C:11](OCC)=[O:12]>>[OH:12][C:11]1[C:10]([OH:16])=[N:9][C:4]2[C:5](=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[N:8]=1

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 1645844-Fluorobenzene-1,2-diamine

Product 1

HCID 178517187HCID 178517187, compound

Procedure

A mixture consisting of 26.3 g. (0.19 mole) of 4-fluoro-1,2-phenylenediamine [Journal of the American Chemical Society, Vol. 75, P. 1294 (1953)] and 150 ml. of diethyl oxalate was refluxed under a nitrogen atmosphere for a period of 18 hours. Upon completion of this step, the reaction mixture was cooled to room temperature (~20° C.), filtered and the recovered product subsequently washed with four-100 ml. portions of ethanol and air-dried to constant weight to ultimately afford 19.3 g. (80%) of pure 2,3-dihydroxy-6-fluoroquinoxaline, m.p. >300° C. (literature m.p. 387°-390° C., according to U.S. Pat. No. 3,992,378). Mass Spectrum: m/e, 180 (P+).

Workup

  1. filtrationfiltered
  2. washthe recovered product subsequently washed with four-100 ml
  3. dry with materialportions of ethanol and air-dried to constant weight to ultimately afford 19.3 g

Sources & evidence

ORD record
ord-781de3fb9a284add8999de14815f3add
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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