2-n-Butyl-4-chloro-5-methoxymethyl-1-(4-nitrobenzyl)imidazole → 1-(4-Aminobenzyl)-2-n-butyl-4-chloro-5-(methoxymethyl)imidazole

HRID 466382Notes

Reaction equation

HRID 466382 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:7]([CH2:11][O:12][CH3:13])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:6]2[C:7]([CH2:11][O:12][CH3:13])=[C:8]([Cl:10])[N:9]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 537649382-n-Butyl-4-chloro-5-methoxymethyl-1-(4-nitrobenzyl)imidazole

Product 1

HCID 543139191-(4-Aminobenzyl)-2-n-butyl-4-chloro-5-(methoxymethyl)imidazoleYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-n-butyl-4-chloro-5-methoxymethyl-1-(4-nitrobenzyl)imidazole (11.22 g) in methanol (100 mL) under N2 was carefully added 1.0 g of 10% palladium on charcoal. Hydrogen gas was then bubbled through the solution for 4 hours. The solution was filtered through Celite® and the solvent removed in vacuo to yield 9.23 g of an amber oil. NMR (200 MHz, CDCl3) δ 7.99 (s, 1H); 6.78 (d of d, 4H, J=5,5 Hz); 5.05 (s, 2H); 4.24 (s, 2H); 3.27 (s, 3H); 2.59 (t, 2H, J=7 Hz); 1.62 (t of t, 2H, J=7,7 Hz); 1.32 (t of q, 2H, J=7,7 Hz); 0.84 (t, 3H,J=7 Hz). Mass Calcd. for C16H23ClN3O; 307.1451. Found: 307.1460.

Workup

  1. customHydrogen gas was then bubbled through the solution for 4 hours
  2. filtrationThe solution was filtered through Celite®
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-90761f776ecb4e05b91726f343862179
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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