Nitric Acid → HCID 178512464, compound

HRID 1359013Notes

Reaction equation

HRID 1359013 reaction equation
[N:1]#[C:2][NH2:3].[NH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2.[N+:14]([O-:17])([OH:16])=[O:15]>O.C(O)C>[N+:14]([O-:17])([OH:16])=[O:15].[NH:4]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)[C:2]([NH2:3])=[NH:1]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 9864Cyanamide2×HCID 788675-Aminoindole

Product 1

HCID 178512464HCID 178512464, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A freshly prepared solution of cyanamide (0.48 g, 11.43 mmol) in water (1 ml) was added to a solution of 5-aminoindole (1.00 g, 7.56 mmol) in ethanol (5 ml). The mixture was treated with concentrated nitric acid (69%, 0.51 ml, 7.90 mmol) and then refluxed for 18 h. A further quantity of cyanamide (0.24 g, 5.71 mmol) was added and then heating continued for 5 h. The reaction mixture was cooled to room temperature and evaporated in vacuo. The residue was triturated with ethyl acetate and the resulting precipitate collected and washed with ethyl acetate, then diethyl ether to give 5-guanidinoindole nitrate (1.67 g) as a brown solid m.p. 132-134°. δH (d6DMSO) 6.46 (1H, s), 6.92 (1H, dd, J 1.8, 8.5 Hz), 7.07 (4H, s), 7.43 (3H, m), 9.35 (1H, s) and 11.25 (1H, br s).

Workup

  1. temperaturerefluxed for 18 h
  2. temperatureheating
  3. customevaporated in vacuo
  4. customThe residue was triturated with ethyl acetate
  5. customthe resulting precipitate collected
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-7b15c9c34f6f4d46b4b3f9f856a388cd
Source dataset
uspto-grants-2003_07
Patent number
US06599908B1

Reaction notes

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