Hydrochloric Acid → HCID 178469838, compound

HRID 1489615Notes

Reaction equation

HRID 1489615 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[NH2:15])=[O:5])[CH3:2].[N:16]#[C:17][NH2:18].[ClH:19]>O1CCOCC1>[ClH:19].[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[NH:15][C:17]([NH2:18])=[NH:16])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 1476606ethyl 2-amino-1H-indole-3-carboxylate

Product 1

HCID 178469838HCID 178469838, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 2 aminoindole-3-carboxylic acid ethyl ester (2.04 g, 10.0 mmol), cyanamide (534 mg, 12.7 mmol), and concentrated hydrochloric acid (1 mL) in dioxane (91 mL), are heated under reflux for 48 hr. After the reaction mixture has cooled to 25 C. it is filtered and the solids washed well with dry diethyl ether, and then air dried to give 2-guanidinoindole-3-carboxylic acid ethyl ester hydrochloride (1.08g, 38%) 2-guanidinoindole-3-carboxylic acid ethyl ester hydrochloride as an off-white solid, mp>250 C.

Workup

  1. temperatureare heated
  2. temperatureunder reflux for 48 hr
  3. temperatureAfter the reaction mixture has cooled to 25 C
  4. filtrationit is filtered
  5. washthe solids washed well with dry diethyl ether
  6. customair dried

Sources & evidence

ORD record
ord-4c80195cae5d447b88ba8ce2e506ffc5
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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