Hydrochloric Acid → HCID 178469838, compound

HRID 1358296Notes

Reaction equation

HRID 1358296 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 (1.08 g, 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-7de335581ce44cc7b027b492dca8c258
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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