Nitric Acid → HCID 178468909, compound

HRID 859100Notes

Reaction equation

HRID 859100 reaction equation
[N+:1]([O-])([OH:3])=[O:2].[CH2:5]([O:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)[CH3:6].[N:17]#[C:18][NH2:19]>C(O)C>[N:1]([OH:3])=[O:2].[CH2:5]([O:7][C:8]([C:9]1[CH:10]=[C:11]([NH:15][C:18]([NH2:19])=[NH:17])[CH:12]=[CH:13][CH:14]=1)=[O:16])[CH3:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 9864CyanamideHCID 11400Ethyl 3-aminobenzoate

Product 1

HCID 178468909HCID 178468909, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Nitric acid (70%, 6.66 mL) is added to a mixture of 3-amino benzoic acid ethyl ester (17.21 g, 104 mmol) and cyanamide (50% in water, 12.1 mL, 156 mmol) in 50 mL of ethanol. The reaction mixture is heated for 24 hours under reflux. It is then cooled to room temperature and filtered. The solid is washed with water, ether and dried to give 3-ethoxycarbonyl-phenyl-guanidine nitrite as a gray solid; ESI-MS (m/z): 208.1 (M+-HNO3+H).

Workup

  1. temperatureThe reaction mixture is heated for 24 hours
  2. temperatureunder reflux
  3. filtrationfiltered
  4. washThe solid is washed with water, ether
  5. customdried

Sources & evidence

ORD record
ord-4f42fc89c4d24dcf89d4fbaf2853fb0d
Source dataset
uspto-grants-2006_12
Patent number
US07151096B2

Reaction notes

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