1-(2-(P-NO2Phenoxy)ethyl)imidazole → 4-[2-(1H-Imidazol-1-yl)ethoxy]aniline

HRID 2415295Notes

Reaction equation

HRID 2415295 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:6][CH:5]=1)([O-])=O.ClCCl.CCOCC>C(O)C.[Pd]>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 2

HCID 135691861-(2-(P-NO2Phenoxy)ethyl)imidazoleHCID 21881112Ethyl ether methylene chloride

Product 1

HCID 135692034-[2-(1H-Imidazol-1-yl)ethoxy]anilineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogenation of the nitro compound (Step A above) in ethanol with 10% palladium on carbon at 2 atmospheres pressure gave, after filtration, evaporation, and crystallization from dichloromethane/ether, 75% yield of 4-(2-imidazol-1-yl-ethoxy)-phenylamine as a light orange solid, mp 93-94° C. Mass spectrum (LR-APCI) MH+=203.

Sources & evidence

ORD record
ord-d0925e5154324f44adc719014dcd8b02
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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