Nitric Acid → 4-Amidino-2-nitrophenol hydrochloride

HRID 517313

Reaction equation

HRID 517313 reaction equation
[ClH:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].[N+:12]([O-])([OH:14])=[O:13].C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O>[ClH:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 217124Benzenecarboximidamide, 4-hydroxy-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 1363523104-Amidino-2-nitrophenol hydrochloride

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Amidinophenol hydrochloride (1.0 g, 5.8 mmol) was dissolved in concentrated sulfuric acid (2.5 mL), and concentrated nitric acid (0.38 mL) was added at −15° C. The reaction mixture was stirred for 1 hour while maintaining the temperature of the reaction mixture at −15° C. to −2° C., and slowly added to ice water. The mixture was neutralized by slowly adding sodium hydrogen carbonate, and the precipitated orange solid was collected by filtration. The solid was washed with water and acetone, and suspended in methanol. 4N Hydrochloric acid/dioxane was added to dissolve the solid. Diisopropyl ether was added to the solution, and the precipitated solid was collected by filtration. The solid was washed with diisopropyl ether and dried to give the title compound (0.98 g) as a pale-yellow powder.

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture at −15° C. to −2° C.
  2. filtrationthe precipitated orange solid was collected by filtration
  3. washThe solid was washed with water and acetone
  4. addition4N Hydrochloric acid/dioxane was added
  5. dissolutionto dissolve the solid
  6. additionDiisopropyl ether was added to the solution
  7. filtrationthe precipitated solid was collected by filtration
  8. washThe solid was washed with diisopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-713ed981356d495f835d656758eebf93
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Linked notes

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