2-(4-Fluorophenyl)-3-(5-methyl-2-nitrophenyl)propanenitrile → 3-(4-Fluorophenyl)-6-methyl-1,2,3,4-tetrahydroquinoline

HRID 717759Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-])=O)[C:9]#N)=[CH:4][CH:3]=1>C1COCC1.CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:11][C:12]3[C:13](=[CH:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)[NH:19][CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-(4-fluorophenyl)-3-(5-methyl-2-nitrophenyl)propanenitrile (0.3 g, 0.00105 mol), and 10% Pd on 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), the catalyst was removed by filtration through Celite. The filtrate was concentrated under reduced pressure, and the product was purified by column chromatography (4% 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 (0.080 g, 33% yield).

Workup

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

Sources & evidence

ORD record: ord-e731d41e26974a808bce0fb6a5e6223a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193728B2

Reaction notes

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