{3-[(Cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methanol → 3-[(Cyclopentylmethyl)(ethyl)amino]-6-methoxypicolinaldehyde

HRID 906323Notes

Reaction equation

[CH:1]1([CH2:6][N:7]([CH2:18][CH3:19])[C:8]2[C:9]([CH2:16][OH:17])=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:1]1([CH2:6][N:7]([CH2:18][CH3:19])[C:8]2[C:9]([CH:16]=[O:17])=[N:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of {3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methanol (2.0 g, 7.57 mmol) in chloroform (200 mL) was added with manganese dioxide (20 g, 230 mmol), and the mixture was stirred at 55° C. for 16 hours. The reaction mixture was filtered through Celite, and the filtrate was washed with chloroform, and then concentrated under reduced pressure. The resulting residue was added with chloroform (200 mL) and manganese dioxide (20 g, 230 mmol), and the mixture was stirred at 55° C. for 6 hours. The reaction mixture was filtered through Celite, and the filtrate was washed with chloroform, and then concentrated under reduced pressure to obtain 3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypicolinaldehyde (1.68 g, 85%) as pale yellow oil.

Workup

filtrationThe reaction mixture was filtered through Celite
washthe filtrate was washed with chloroform
concentrationconcentrated under reduced pressure
stirringthe mixture was stirred at 55° C. for 6 hours
filtrationThe reaction mixture was filtered through Celite
washthe filtrate was washed with chloroform
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-15d97ace52534fe782c3b1287843c509
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012989B2

Reaction notes

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