Glyoxylic Acid → HCID 178516718, compound

HRID 2163505Notes

Reaction equation

HRID 2163505 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[CH:4][CH:3]=1.CO.[C:14](O)(=O)[CH:15]=[O:16]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[N:8]=[C:15]([OH:16])[CH:14]=[N:9]2

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 887MethanolHCID 698552-Chloro-6-nitroaniline

Product 1

HCID 178516718HCID 178516718, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

100 ml of triethylamine were added to the reduction product of 6-chloro-2-nitroaniline in methanol (assumed to be 8 mol), obtained as described under (a). The mixture was then heated to 50° C. 1,168 g (8 mol) of glyoxylic acid semiacetal ester were then added dropwise, over the course of 2 hours, to the mixture, thereby causing a slight exothermic reaction. The mixture was boiled for 2 hours under reflux, whereupon a solid product separated out. After 2 hours, the mixture was cooled to 0° C. and the precipitate was filtered off. 110 g (7.6% of theory) of 8-chloro-2-hydroxy-quinoxaline were obtained in the form of a light gray powder of melting point above 250° C. The mother liquor was concentrated, ether was added and the residue was filtered off. A further 583 g (40.6% of theory) were thus obtained. Accordingly, the total yield was 693 g (48% of theory). ##STR30##

Workup

  1. customobtained
  2. customa slight exothermic reaction
  3. temperatureunder reflux, whereupon a solid product
  4. customseparated out
  5. waitAfter 2 hours
  6. temperaturethe mixture was cooled to 0° C.
  7. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-ca28fe0731e64917881fdc190b5646f8
Source dataset
uspto-grants-1979_01
Patent number
US04134978

Reaction notes

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