Hydrochloric Acid → HCID 178526472, compound

HRID 437142Notes

Reaction equation

HRID 437142 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].O.O.[C:14](O)(=[O:18])[C:15](O)=[O:16].Cl>>[OH:16][C:15]1[C:14]([OH:18])=[N:11][C:6]2[C:7](=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 61373Oxalic acid dihydrateHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 178526472HCID 178526472, compoundYield 74.6%

Procedure

A mixture of 225 g (1.47 moles) of 4-nitro-o-phenylenediamine, 375 g. (2.97 moles) of oxalic acid dihydrate and 2250 ml. of 6 N hydrochloric acid is combined in a 3 necked 5 liter round bottom flask which is fitted with a reflux condenser and a teflon paddle stirrer. The suspension is heated at reflux temperature for one hour and allowed to stand at room temperature over night. The material is filtered and the dark brown solid collected is washed with five 300 ml. portions of hot distilled water. The solid is slurried in two equal portions each in 40 ml. of 2 N sodium hydroxide. Each mixture is heated to near boiling with stirring and filtered hot. The red-brown hot filtrate is treated with about two liters of 4 N hydrochloric acid for each batch and the slightly acidic mixtures are filtered while still hot. The brown solid collected is washed with water several times, air dried and finally dried in vacuo over phosphorous pentoxide at 78° C. to give 227.2 g of 2,3-dihydroxy-6-nitroquinoxaline. The reference for the above compound is H. I. X. Mager and W. Berends, Rec. Trav. Chim. 78, 5-21 (1959). An additional reference is F. H. S. Curd, D. G. Davey, and G. J. Stacy, Journ. Chem. Soc. 275, 1271-1277 (1949).

Workup

  1. customis fitted with a reflux condenser and a teflon paddle stirrer
  2. temperatureThe suspension is heated
  3. temperatureat reflux temperature for one hour
  4. waitto stand at room temperature over night
  5. filtrationThe material is filtered
  6. customthe dark brown solid collected
  7. washis washed with five 300 ml
  8. distillationportions of hot distilled water
  9. temperatureEach mixture is heated
  10. filtrationfiltered hot
  11. additionThe red-brown hot filtrate is treated with about two liters of 4 N hydrochloric acid for each batch
  12. filtrationthe slightly acidic mixtures are filtered while still hot
  13. customThe brown solid collected
  14. washis washed with water several times, air
  15. customdried
  16. dry with materialfinally dried in vacuo over phosphorous pentoxide at 78° C.

Sources & evidence

ORD record
ord-9eb1a444694243faba25437cc31cbb76
Source dataset
uspto-grants-1977_06
Patent number
US04029788

Reaction notes

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