Methanol → Diazomethane

HRID 1899592

Reaktionsgleichung

Reaktionsgleichung von HRID 1899592
[CH3:1][N:2]([N:9]=O)C(N[N+]([O-])=O)=N.[OH-].[K+].CO.[CH2:15]([N:18]([CH2:35][CH2:36][CH3:37])[CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([C:29]3[CH:33]=[C:32]([OH:34])[NH:31][N:30]=3)[CH:23]=[CH:24][CH:25]=2)[CH2:20]1)[CH2:16][CH3:17]>CCOCC>[N+:2](=[CH2:1])=[N-:9].[CH2:35]([N:18]([CH2:15][CH2:16][CH3:17])[CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([C:29]3[CH:33]=[C:32]([O:34][CH3:1])[NH:31][N:30]=3)[CH:23]=[CH:24][CH:25]=2)[CH2:20]1)[CH2:36][CH3:37]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidineHCID 178457149HCID 178457149, Verbindung

Produkt 2

HCID 9550DiazomethaneHCID 178457148HCID 178457148, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 20 mmol diazomethane was prepared by adding 4.29 g (29 mmol) 1-methyl-3-nitro-1-nitrosoguanidine to a 25% solution KOH (10 ml) and Et2O (30 ml) in an ice bath. The ethereal phase was decanted into a solution of 25 ml methanol containing 400 mg (1.28 mmol) of 2-di-n-propylamino-8-(5-hydroxypyrazol-3-yl)-1,2,3,4-tetrahydronaphthalene. The title compound was isolated by concentrating the reaction and purifying the 500 mg of brown oil crude by flash column chromatography eluting with 9:1 mixture of methylene chloride and methanol. 190 mg were collected. The correct mass of 328 was found using FAB spectrum.

Quellen und Nachweise

ORD-Eintrag
ord-9e894e70ea054042bcf37fc5cd74245c
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05571942

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