(4-Nitrophenyl)[2-(1-propyl)imidazolyl]methanol → HCID 178440138, compound

HRID 856781Notes

Reaction equation

HRID 856781 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][CH3:19])[NH:15][CH:16]=2)[OH:11])=[CH:6][CH:5]=1)([O-])=O>CO.C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][CH3:19])[NH:15][CH:16]=2)[OH:11])=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 178440139(4-Nitrophenyl)[2-(1-propyl)imidazolyl]methanol

Product 1

HCID 178440138HCID 178440138, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a mixed solution of (4-nitrophenyl)[2-(1-propyl)imidazolyl]methanol (4.5 g) in methanol (150 ml) and ethanol (100 ml), 10% palladium carbon (450 mg) was added, and the mixture was stirred for 4 hours under hydrogen atmosphere. The insolubles were filtered off, and the residue was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8) and recrystallized from ethyl acetate-diisopropyl ether, to give (4-aminophenyl)[2-(1-propyl)imidazolyl]methanol (3.52 g) as brown crystals.

Workup

  1. filtrationThe insolubles were filtered off
  2. customthe residue was purified by basic silica gel column chromatography (methanol-ethyl acetate=1:8)
  3. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-0aa2d15d811b4c3390a3f0771736ea37
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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