4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-(1-imidazolyl)phenyl)-1H-imidazole → 1-(2-amino-5-(1-imidazolyl)phenyl)-4-ethoxycarbonyl-5-methyl-1H-imidazole

HRID 1599431Notes

Reaction equation

HRID 1599431 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:12]2[CH:17]=[C:16]([N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)[CH:15]=[CH:14][C:13]=2[N+:23]([O-])=O)[C:10]=1[CH3:11])=[O:5])[CH3:2]>C(O)C.[Pd]>[NH2:23][C:13]1[CH:14]=[CH:15][C:16]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)=[CH:17][C:12]=1[N:9]1[C:10]([CH3:11])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=[CH:8]1

Participants

4

Reactant 1

HCID 189281334-ethoxycarbonyl-5-methyl-1-(2-nitro-5-(1-imidazolyl)phenyl)-1H-imidazole

Product 1

HCID 189281051-(2-amino-5-(1-imidazolyl)phenyl)-4-ethoxycarbonyl-5-methyl-1H-imidazoleYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-(1-imidazolyl)phenyl)-1H-imidazole (14 g, 41 mmol) in ethanol (1.0 l) was hydrogenated in a PARR hydrogenation apparatus at 30 psi and 25° C. using 1.0 g 5% Pd-C as a catalyst. The reaction mixture was filtered and concentrated in vacuo to give 12.4 g (98%) of 1-(2-amino-5-(1-imidazolyl)phenyl)-4-ethoxycarbonyl-5-methyl-1H-imidazole.

Workup

  1. customwas hydrogenated in a PARR hydrogenation apparatus at 30 psi and 25° C.
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28e229f82c6d423a9577bf7c6b45b45e
Source dataset
uspto-grants-1998_04
Patent number
US05741785

Reaction notes

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