Acetic Acid → Ethyl 1-(5-chloro-2-pyridinyl)-1H-imidazole-4-carboxylate

HRID 397940Notes

Reaction equation

HRID 397940 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[CH:9]([O:16][CH2:17][CH3:18])([O:13]CC)OCC.[N+:19]([CH2:22][C:23](OCC)=O)([O-])=O.[C:28](O)(=O)C>[Fe]>[CH2:17]([O:16][C:9]([C:22]1[N:19]=[CH:28][N:1]([C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=2)[CH:23]=1)=[O:13])[CH3:18]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 661742-Amino-5-chloropyridineHCID 69379Ethyl nitroacetate

Product 1

HCID 53752991Ethyl 1-(5-chloro-2-pyridinyl)-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 384, 2-amino-5-chloropyridine was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid. After workup and chromatography the title compound was obtained as a beige crystalline solid. Mp. 163-164° C. (AcOEt), MS: m/e=252 (M+H+).

Sources & evidence

ORD record
ord-782f3ba2bde242fe9941911d915a2432
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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