Imidazole → 1-(4-Cyanobenzyl)-2-methylimidazole-5-carboxaldehyde

HRID 342152Notes

Reaction equation

HRID 342152 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:18])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[C:6]=1[CH:7]=[O:8].N1C=CN=C1.[H][H]>[Pd]>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:5]2[C:6]([CH:7]=[O:8])=[CH:2][N:3]=[C:4]2[CH3:18])=[CH:11][CH:12]=1)#[N:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 226259164-Bromo-1-(4-cyanobenzyl)-2-methylimidazole-5-carboxaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 153910091-(4-Cyanobenzyl)-2-methylimidazole-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 4-bromo-1-(4-cyanobenzyl)-2-methylimidazole-5-carboxaldehyde (1.33 g, 4.37 mmol) and imidazole (0.600 g, 8.74 mmol) in 1:1 ethyl acetate-alcohol (150 mL) was stirred with 10% palladium on carbon (0.020 g) under 1 atm hydrogen. After 2 h, the reaction was filtered through celite and concentrated to give the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.62 (1H, s), 7.90 (1H, s), 7.81 (2H, d, J=8 Hz), 7.20 (2H, d, J=8 Hz), 5.64 (2H, s), 2.33 (3H, s).

Workup

  1. filtrationthe reaction was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f969ce93ef8a44b285bcf16e995617b4
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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