Hydrochloric Acid → 4-Hydroxy-3-nitrobenzene-1-carboximidamide

HRID 1981432Notes

Reaction equation

HRID 1981432 reaction equation
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].Cl.[N+:13]([O-])([OH:15])=[O:14].C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O>[C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)(=[NH:3])[NH2:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 217124Benzenecarboximidamide, 4-hydroxy-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 1355987304-Hydroxy-3-nitrobenzene-1-carboximidamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 20 ml of concentrated sulfuric acid, was added 7.6 g of 4-amidinophenol hydrochloride. When the evolution of hydrogen chloride gas had ceased, the solution was cooled in an ice-salt bath and 3.0 ml of nitric acid was slowly added to the solution while being stirred. The mixture was then stirred at room temperature for 20 to 30 minutes. The reaction mixture, orange in color, was diluted by pouring into a large volume of ice water. The diluted solution was added in small portions to a saturated aqueous sodium hydrogencarbonate solution to precipitate orange needle crystals. The crystals were collected by filtration and dried to obtain 7.6 g of 4-amidino-2-nitrophenol.

Workup

  1. temperaturethe solution was cooled in an ice-salt bath
  2. stirringThe mixture was then stirred at room temperature for 20 to 30 minutes
  3. additionThe reaction mixture, orange in color, was diluted
  4. customto precipitate orange needle crystals
  5. filtrationThe crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-fcd5babde79144f3a63e03e75c6ff2a4
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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