HCID 67373307, compound → HCID 67371330, compound

HRID 717751Notes

Reaction equation

HRID 717751 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-])=O)=[C:6]([CH2:8][CH:9]([C:12]2[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[C:10]#N)[CH:7]=1>C1COCC1.CO.[C].[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:19][CH2:10][CH:9]([C:12]1[CH:13]=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=1)[CH2:8]2

Participants

5

Reactant 1

HCID 67373307HCID 67373307, compound

Product 1

HCID 67371330HCID 67371330, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-(5-methyl-2-nitrophenyl)-2-(6-methylpyridin-3-yl)propanenitrile (0.3 g, 0.00106 mol), 10% palladium carbon (0.180 g) in THF (1 mL) and MeOH (6 mL) was stirred under atmospheric hydrogen pressure at 40° C. for 24 h. After completion of reaction (monitored by TLC), catalyst was removed by filtration through Celite, and the filtrate concentrated under reduced pressure. The product was purified by column chromatography (25% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to give the desired compound as a yellow colored solid (0.075 g, 30% yield).

Workup

  1. customAfter completion of reaction (monitored by TLC), catalyst
  2. customwas removed by filtration through Celite
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe product was purified by column chromatography (25% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch)

Sources & evidence

ORD record
ord-ae635065ab464ca585b0fa470eb21b42
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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