Ammonium Hydroxide → 5-Chloropyridine-2-carboxamide

Temperature

80 °C

A 500-mL RBF was charged with 5-chloro-2-pyridinecarboxylic acid (Ark Pharm, 10.00 g, 63.5 mmol) and thionyl chloride (Aldrich, 100 ml, 1371 mmol). A catalytic amount of DMF (0.2 ml) was added and the reaction mixture was heated to 80° C. under Argon atmosphere for 4 hours. The reaction mixture was cooled to RT and concentrated under reduced pressure. The residue was diluted with DCM (100 ml) and added slowly to a stirred solution of ammonium hydroxide (131 ml, 3364 mmol) at 0° C. After completed addition, the reaction mixture was allowed to stir an additional 10 min. The reaction mixture was concentrated under reduced pressure and the precipitate was filtered off. The solid was washed with water and dried to give the title compound (8.686 g, 55.5 mmol, 87% yield) as an off-white solid. MS m/z=157 [M+H]+. Calculated for C6H5ClN2O: 156

1. temperatureThe reaction mixture was cooled to RT
2. concentrationconcentrated under reduced pressure
3. additionThe residue was diluted with DCM (100 ml)
4. additionaddition
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. filtrationthe precipitate was filtered off
7. washThe solid was washed with water
8. customdried

ORD record

ord-beb9c151000d447889741f34afea5da5

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2