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

HRID 435883Notes

Reaction equation

HRID 435883 reaction equation
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

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 12509100HCID 12509100, compound2×HCID 125091131-(2-Methoxy-5-nitrophenyl)-1H-imidazole

Product 1

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

Procedure

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.

Sources & evidence

ORD record
ord-c9bc556ecae5434d988c12d88d0783bd
Source dataset
uspto-grants-1977_02
Patent number
US04006243

Reaction notes

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