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

HRID 397922Notes

Reaction equation

HRID 397922 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-0adcc3ee905e4f5495fbea9c23ee5369
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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