Picolinic acid → 4-Chloro-N,N-diisopropylpicolinamide

温度

45 °C

Thionyl chloride (60 ml, 823 mmol) was diluted with toluene (100 ml) and heated to 45° C. To the mixture, N,N-dimethylformamide (16 ml, 207 mmol) was added and the resultant mixture was stirred in the same conditions for one hour. To the mixture, picolinic acid (25 g, 203 mmol) was added and the resultant mixture was stirred at 80° C. for one hour and 20 minutes. After the reaction mixture was concentrated and diisopropylamine (185 ml, 807 mmol) and acetonitrile (500 ml) were added to the residue, the mixture was stirred at room temperature for 21 hours and 30 minutes. After the reaction mixture was concentrated, the residue was separated with ethyl acetate and water. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, filtrated and concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (31.1 g, yield: 63.6%) as a pale brown solid.

1. concentrationAfter the reaction mixture was concentrated
2. concentrationAfter the reaction mixture was concentrated
3. customthe residue was separated with ethyl acetate and water
4. washThe organic layer was washed with a saturated saline solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltrated
7. concentrationconcentrated
8. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

ORDレコード

ord-8661001b7c3a4f4b9fc5ffc76535e38c

出典データセット

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08124780B2