Reaktion #652191

Reaktionsgleichung

methyl 1-methyl-2-indole-carboxylate

guanidine hydrochloride

sodium methoxide

→

1-methyl-2-indoloylguanidine

1-methyl-2-indoloylguanidine hydrochloride

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe precipitated sodium chloride was filtered off
2. 2
   Sonstigeto obtain the solution
3. 3
   workup.DISTILLATIONSubsequently methanol was distilled off under reduced pressure
4. 4
   TemperaturThe resulting residue was heated at 130° C. for 5 minutes
5. 5
   workup.WAITto stand at room temperature for an hour
6. 6
   workup.ADDITIONThereafter water was poured onto the reaction solution
7. 7
   Extraktionthe mixture was extracted three times with ethyl acetate
8. 8
   WaschenThe combined extracts were washed with water
9. 9
   TrocknenAfter drying over anhydrous magnesium sulfate
10. 10
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
11. 11
    SonstigeThe resulting residue was isolated
12. 12
    Sonstigepurified by silica gel column chromatography

Vorschrift

After 8.58 g (89.8 mmol) of guanidine hydrochloride was added to 70 ml of a methanol solution of 4.85 g (89.8 mmol) of sodium methoxide, the mixture was stirred at room temperature. The precipitated sodium chloride was filtered off to obtain the solution. Then 1.70 g (8.97 mmol) of methyl 1-methyl-2-indole-carboxylate was added to the thus obtained solution. Subsequently methanol was distilled off under reduced pressure. The resulting residue was heated at 130° C. for 5 minutes and then allowed to stand at room temperature for an hour. Thereafter water was poured onto the reaction solution and the mixture was extracted three times with ethyl acetate. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was isolated and purified by silica gel column chromatography to give the desired 1-methyl-2-indoloylguanidine. The compound was dissolved in chloroform and treated with hydrogen chloride/ether. Thus 0.70 g (30.8%) of 1-methyl-2-indoloylguanidine hydrochloride was obtained.

Quelle