HCID 18957764, compound → HCID 18957761, compound

HRID 2379373Notes

Reaction equation

HRID 2379373 reaction equation
[CH3:1][C:2]([CH3:23])([O:4][C:5]([N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=1)=[CH2:13])=[O:6])[CH3:3]>C(O)C.[Pd]>[CH3:23][C:2]([CH3:1])([O:4][C:5]([N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1)[CH3:13])=[O:6])[CH3:3]

Participants

4

Reactant 1

HCID 18957764HCID 18957764, compound

Product 1

HCID 18957761HCID 18957761, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(1,1-dimethylethyloxycarbonyl)-2-((3-nitrophenyl)ethen-2-yl)imidazole (500 mg, 1.59 mmol)in ethanol (50 ml) was hydrogenated at 30 psi in the presence of 10% palladium-on-carbon (50 mg) for 1 h. The catalyst was then removed by filtration and the solvent evaporated to afford the titled compound as a viscous oil (340 mg, 75% yield). 1H NMR (250 MHz, CDCl3) δ 1.60 (9H, s), 2.92-3.04 (2H, m), 3.22-3.36 (2H, m), 3.70 (2H, brs), 6.42-6.68 (3H, m), 6.87 (1H, d, J =2.5 Hz), 7.05 (1H, t, J=8 Hz), 7.32 (1H, d, J=2.5 Hz).

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-a4d9902022f4402a81fa92e404666c8e
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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