Nitric Acid → HCID 178512464, compound

HRID 1106567Notes

Reaction equation

HRID 1106567 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-68e8d595aac14d7ba6567ef317482eb4
Source dataset
uspto-grants-2000_05
Patent number
US06057329

Reaction notes

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