Oxalic acid dihydrate → HCID 178527601, compound

HRID 1165807Notes

Reaction equation

HRID 1165807 reaction equation
[NH2:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12]([OH:15])(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:16].O.O.[C:19](O)(=[O:23])[C:20](O)=[O:21]>Cl>[OH:21][C:20]1[C:19]([OH:23])=[N:16][C:3]2[CH:4]=[CH:5][C:6]3[C:7]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 665451-Naphthalenesulfonic acid, 5,6-diamino-

Product 1

HCID 178527601HCID 178527601, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 0,5 g (2,1 mmol) 1,2-diaminonaphthalene-5-sulphonic acid and 0,75 g (5,8 mmol) oxalic acid dihydrate in 25 ml 4N hydrochloric acid was refluxed for 4 h. After cooling to 25° C., the precipitate was filtered off and washed with 5 ml 4N hydrochloric acid and 5 ml ice-cooled water. The crude product was dissolved in 15 ml 4N sodium hydroxide, and then reprecipitated with 4N hydrochlorid acid to give 0,35 g (57%) of 2,3-dihydroxy-benzo(f)quinoxaline-7-sulphonic acid, m.p. > 300° C. IR (KBr): 3450 (m), 1690 (s), 1190 (s), 1055 (s), 1020 (s) cm-1.1H NMR (DMSO-d6): 12,2 (2H,s), 8,7 (1H,d), 8,6 (1H,d), 8,0 (1H,d), 7,5 (1H,t), 7,4 (1H,d).

Workup

  1. temperaturewas refluxed for 4 h
  2. filtrationthe precipitate was filtered off
  3. washwashed with 5 ml 4N hydrochloric acid and 5 ml ice-
  4. temperaturecooled water
  5. dissolutionThe crude product was dissolved in 15 ml 4N sodium hydroxide
  6. customreprecipitated with 4N hydrochlorid acid

Sources & evidence

ORD record
ord-439f9300ee4947cd9e26d49d7890b3f6
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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