Dimethylformamide → 2,6-Dichloropyridine-3-carboxamide

A suspension of 2,6-dichloronicotinic acid (5 g, 26.0 mmol) in CH2Cl2 (20 mL) was treated with oxalyl dichloride (3.97 g, 31.3 mmol) and few drops of DMF, and stirred at rt. The generation of bubbles was observed and the reaction mixture gradually became clear. The resulting clear solution was concentrated on a rotary evaporator to remove traces of oxalyl chloride, dissolved in CH2Cl2 (20 mL), treated with aqueous NH4OH (3.47 mL, 52.1 mmol) added drop-wise, and stirred at rt for 1 h. The resulting mixture was diluted with CH2Cl2 (white precipitate doesn't all dissolve), washed with satd. NaHCO3, and concentrated to obtain 2.97 g of 2,6-dichloronicotinamide as a white solid. LCMS: (M+H)+=190.96 (100%) 192.93 (70%) 194.93 (20%).

1. concentrationThe resulting clear solution was concentrated on a rotary evaporator
2. customto remove traces of oxalyl chloride
3. dissolutiondissolved in CH2Cl2 (20 mL)
4. additionadded drop-wise
5. stirringstirred at rt for 1 h
6. dissolutionall dissolve),
7. washwashed with satd
8. concentrationNaHCO3, and concentrated

ORD record

ord-8e37dfffac5b44af9f3af7da1c5a7d57

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586751B2