Nitric Acid → 3-Nitrophenylguanidine Nitrate

HRID 47198

Reaction equation

HRID 47198 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[N+:11]([O-:14])([OH:13])=[O:12].[N:15]#[C:16][NH2:17]>CCO>[N+:11]([O-:14])([OH:13])=[O:12].[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:16]([NH2:17])=[NH:15])[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 74233-NitroanilineHCID 9864Cyanamide

Product 1

HCID 1785125133-Nitrophenylguanidine NitrateYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-nitroaniline (50 mmol, 6.90 g) in EtOH (10 mL) was cooled on an ice bath. Nitric acid (69% aq. soln.; 3.6 mL) was added dropwise. To this mixture cyanamide (50% aq soln.; 5 mL) was added. The reaction mixture was stirred at r.t. for 10 min and was then refluxed under N2 for a further 22 h. The solvent was evaporated. The dark brown solid was washed with EtOAc/EtOH and dried-under high vacuum overnight to afford the title compound as a brown solid (6.90 g, 57%). 1H-NMR (300 MHz, DMSO-d6) δ7.66-7.75 (m, 2H, Ph-H), 8.09-8.14 (m, 2H, Ph-H).

Workup

  1. temperaturewas cooled on an ice bath
  2. temperaturewas then refluxed under N2 for a further 22 h
  3. customThe solvent was evaporated
  4. washThe dark brown solid was washed with EtOAc/EtOH and dried-under high vacuum overnight

Sources & evidence

ORD record
ord-22913f1654784eeab53d85fc59c0827c
Source dataset
uspto-grants-2004_03
Patent number
US06699854B2

Linked notes

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