Nitric Acid → 2-(1H-Imidazol-1-yl)-4-nitrophenol

Reaktionsgleichung

Cl.C(OC1C=CC=CC=1N1C=CN=C1)C=C.C(OC(=O)C)(=O)C.[N+]([O-])(O)=O.C[O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:31]=1[N:39]1[CH:43]=[CH:42][N:41]=[CH:40]1>>[N:39]1([C:31]2[CH:32]=[C:33]([N+:36]([O-:38])=[O:37])[CH:34]=[CH:35][C:30]=2[OH:29])[CH:43]=[CH:42][N:41]=[CH:40]1

Komponenten

Edukt 4

HCID 944Nitric Acid

HCID 7918Acetic Anhydride

HCID 12509100HCID 12509100, Verbindung2×

HCID 125091131-(2-Methoxy-5-nitrophenyl)-1H-imidazole

Produkt 1

HCID 214815912-(1H-Imidazol-1-yl)-4-nitrophenol

Versuchsvorschrift

2.15 g. of 1-(2-methoxyphenyl)-imidazole (literature citation in Example 56) is nitrated in a mixture of 60 ml. of acetic anhydride and 20 ml. of 65% nitric acid for 2 hours at 10°. By ether splitting (literature citation in Example 56) of the thus-formed 1-(2-methoxy-5-nitrophenyl)-imidazole (1.8 g.; m.p. 139°-140° from methylene chloride/ether), 420 mg. of 2-(1-imidazolyl)-4-nitrophenol is obtained according to the literature citation in Example 56. This product is etherified analogously to Example 56 with the use of 400 mg. of 2,4 -dichlorobenzyl chloride.