Hydrochloric Acid → 2-(4-Aminophenyl)-1-benzyl-4-chloro-5-(hydroxymethyl)imidazole hydrochloride

HRID 896948Notes

Reaction equation

HRID 896948 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][OH:14])=[C:11]([Cl:15])[N:10]=[C:9]1[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>[Pd].O>[ClH:15].[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:12]([CH2:13][OH:14])=[C:11]([Cl:15])[N:10]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15088539(1-benzyl-4-chloro-2-(4-nitrophenyl)-1H-imidazol-5-yl)methanol2×

Product 1

HCID 223457292-(4-Aminophenyl)-1-benzyl-4-chloro-5-(hydroxymethyl)imidazole hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 1-benzyl-4-chloro-5-(hydroxymethyl)-2-(4-nitrophenyl)imidazole (1.0 g, 2.8 mmol, Compound 8 from Example 5), 10% palladium on carbon (0.10 g), 12M HCl (1.0 ml) 96% ethanol (50 ml) and water (50 ml) was hydrogenated at 55 psi for 1.5 hours on a Parr shaker hydrogenation apparatus. The mixture was filtered through a celite pad and then through a fluted filter paper. Evaporation left 1.5 g of amber oil.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. filtrationthrough a fluted filter paper
  3. customEvaporation
  4. waitleft 1.5 g of amber oil

Sources & evidence

ORD record
ord-2a729d693d89453eafa986ef7bd845ce
Source dataset
uspto-grants-2005_07
Patent number
US06921525B2

Reaction notes

Loading…