Picolinic acid → Diethyl 2-(2-methylquinolin-7-yl)malonate

HRID 339075Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:12])=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1C(O)=O.C([O-])([O-])=O.[Cs+].[Cs+].[C:28]([O:36][CH2:37][CH3:38])(=[O:35])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>O1CCOCC1.O.C(OCC)(=O)C>[CH3:12][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:28]([O:36][CH2:37][CH3:38])=[O:35])=[CH:3][CH:4]=2)[N:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 7-bromo-2-methylquinoline (2.00 g, 9.01 mmol), Cu(I)I (0.172 g, 0.90 mmol), picolinic acid (0.222 g, 1.80 mmol), Cs2CO3 (8.80 g, 27.0 mmol) and diethyl malonate (2.73 mL, 18.0 mmol) in dioxane (25 mL) was stirred at 100° C. for hours. After cooling to ambient temperature, ethyl acetate (30 mL) and water (15 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by flash chromatography on silica gel (3:2 hexane/ethyl acetate) to give diethyl 2-(2-methylquinolin-7-yl)malonate (0.7 g, 2.32 mmol, 26% yield) as oil.

Workup

temperatureAfter cooling to ambient temperature
customThe organic layer was separated
washwashed with brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue obtained
customwas purified by flash chromatography on silica gel (3:2 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f254e49f4fea4f2aa859f138dfbcc5e9
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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