(3-Methyl-4-nitrophenyl)methanamine → Ethyl 5-(4-methoxyphenyl)-2-(3-methyl-4-nitrophenyl)-imidazole-4-carboxylate

HRID 1595353Notes

Reaction equation

HRID 1595353 reaction equation
O[N:2]=[C:3]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[CH2:23][NH2:24]>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[NH:24][C:23]([C:22]3[CH:25]=[CH:26][C:27]([N+:28]([O-:30])=[O:29])=[C:20]([CH3:19])[CH:21]=3)=[N:2][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 21704119(3-Methyl-4-nitrophenyl)methanamineHCID 178472900HCID 178472900, compound

Product 1

HCID 178470213Ethyl 5-(4-methoxyphenyl)-2-(3-methyl-4-nitrophenyl)-imidazole-4-carboxylateYield 22.5%

Procedure

Ethyl 2-hydroxyimino-3-(4-methoxyphenyl)-3-oxopropionate (121.6 g) and 3-methyl-4-nitrobenzylamine (105.4 g) were reacted in the same manner as in Starting Material Synthetic Example 1. After the reaction, the solvent was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography to give ethyl 5-(4-methoxyphenyl)-2-(3-methyl-4-nitrophenyl)imidazole-4-carboxylate (41.5 g), melting point 187-191° C.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ef2767185e0e44b4aa1f89d749673adf
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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