Triethylamine → HCID 66664758, compound

Ethyl malonyl chloride (4.29 g, 28 mmol) was added to a solution of methyl 3-amino-4-methylthiophene-2-carboxylate (4 g, 23 mmol) and triethylamine (4.2 mL, 30 mmol) in dichloromethane (50 mL) and the resulting mixture was stirred for 30 minutes. The reaction mixture was diluted with dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. To the oily residue was added a freshly prepared ethanolic solution of sodium ethoxyde (0.5 g in 25 mL of EtOH) and the reaction mixture was heated at reflux overnight. The solvent was evaporated under reduced pressure and water (50 mL) was added to the residue, followed by sodium hydroxide (1.5 g). The resulting mixture was heated at reflux overnight, then was cooled and acidified by addition of an aqueous solution of hydrochloric acid (6 M). The solid formed was collected by filtration, washed with water and dried under reduced pressure to afford 2.0 g of 3-methyl-4H-thieno[3,2-b]pyridine-5,7-dione.

1. washwashed with water and brine
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationfiltered
4. customevaporated under reduced pressure
5. additionTo the oily residue was added a freshly prepared ethanolic solution of sodium ethoxyde (0.5 g in 25 mL of EtOH)
6. temperaturethe reaction mixture was heated
7. temperatureat reflux overnight
8. customThe solvent was evaporated under reduced pressure and water (50 mL)
9. additionwas added to the residue
10. temperatureThe resulting mixture was heated
11. temperatureat reflux overnight
12. temperaturewas cooled
13. additionacidified by addition of an aqueous solution of hydrochloric acid (6 M)
14. customThe solid formed
15. filtrationwas collected by filtration
16. washwashed with water
17. customdried under reduced pressure

ORD record

ord-344c3606bebe4e07b3cff63629a10ae1

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255110B2