Acetic Acid → 1-(3-Bromophenyl)-1H-imidazole-4-carboxylic acid

HRID 1841248Notes

Reaction equation

HRID 1841248 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH:9](OCC)(OCC)OCC.[N+:19]([CH2:22]C(OCC)=O)([O-])=O.[C:28]([OH:31])(=[O:30])[CH3:29]>[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[CH:9]=[C:29]([C:28]([OH:31])=[O:30])[N:19]=[CH:22]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 115623-BromoanilineHCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetate

Product 1

HCID 234449541-(3-Bromophenyl)-1H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 234, 3-bromoaniline was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The title compound was obtained as a light brown crystalline solid. Mp. 205-207° C. (H2O/dioxane), MS: m/e=267 (M−H−).

Sources & evidence

ORD record
ord-7cb7143f5d8c41e8a6e6825030a80257
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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