Dimethylformamide → HCID 53723761, compound

A solution of 10.6 g (52.5 mmol) of 3-carboxy-2-chloro-5-nitro pyridine (J. Med. Chem. 1895, 1992) and 8.86 g (69.8 mmol) of oxalyl chloride was stirred in 200 ml of methylene chloride. About 0.2 ml of N,N-dimethylformamide was added and the mixture was stirred for 5.5 hr. Solvent is removed and the resulting acid chloride was used without additional purification. The acid chloride was dissolved in 163 ml of methylene chloride containing 5.55 g (55.5 mmol) of 3-dimethylamine-acrylonitrile and 7.46 g (57.7 mmol) of diisopropylethyl amine. The solution was refluxed under nitrogen for 16 hr. The mixture was diluted with chloroform and washed with a saturated solution of sodium bicaronate. The organic layer was dried over magnesium sulfate and place on a column of silica gel. The product was eluted with a combination of chloroform and ether. Solvent was removed and the residue was treated with a mixture of ethyl acetate-hexane 1:1 at which time the mixture crystallized. The solid was collected giving 8.9 g of the title compound as an orange solid:: mass spectrum (chemical ionization, m/e): M+H 281.

1. customSolvent is removed
2. customthe resulting acid chloride was used without additional purification
3. temperatureThe solution was refluxed under nitrogen for 16 hr
4. washwashed with a saturated solution of sodium bicaronate
5. dry with materialThe organic layer was dried over magnesium sulfate and place on a column of silica gel
6. washThe product was eluted with a combination of chloroform and ether
7. customSolvent was removed
8. additionthe residue was treated with a mixture of ethyl acetate-hexane 1:1 at which time the mixture
9. customcrystallized
10. customThe solid was collected

ORD record

ord-b75a1bc724b445adbea1b70983cd4661

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06548496B2