Oxalic acid dihydrate → HCID 178509543, compound

HRID 1165822Notes

Reaction equation

HRID 1165822 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]#[N:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:14].O.O.[C:17](O)(=[O:21])[C:18](O)=[O:19]>Cl>[OH:19][C:18]1[C:17]([OH:21])=[N:14][C:3]2[CH:4]=[CH:5][C:6]3[C:7]([C:12]#[N:13])=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 15066359HCID 15066359, compound

Product 1

HCID 178509543HCID 178509543, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 0,6 g (3,3 mmol) 1,2-diamino-5-cyanonaphthalene and 1,4 g oxalic acid dihydrate in 35 ml 0,5N hydrochloric acid was refluxed for 3 h. After cooling to 25° C., the precipitate was filtered off and washed with water. The crude product was recrystallized (dimethylsulfoxide-methanol) to give 0,35 g (45%) 2,3-dihydroxy-7-cyano-benzo[f]quinoxaline, m.p. >300° C. IR (KBr): 2190 cm-1 (nitrile function).

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customThe crude product was recrystallized (dimethylsulfoxide-methanol)

Sources & evidence

ORD record
ord-132005293cd74b12b55193e43468fba2
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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