Ethyl cyanoacetate → HCID 68184401, compound

Temperature

90 °C

To a solution of ethyl cyanoacetate (3.2 mL) in dimethyl sulfoxide (20 mL) was added sodium hydride (1.22 g) at room temperature, and then 1,4-dibromo-2-nitrobenzene (4.21 g) was added, and the reaction mixture was stirred at 90° C. for 3 hours. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was suspended in an aqueous solution of 1M-sodium hydrogen carbonate (60 mL), and the reaction mixture was stirred at 80° C. for 24 hours. To the reaction mixture was added 2N-hydrochloric acid, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (20 mL), ethanol (40 mL) and water (20 mL). To the solution were added ammonium chloride (4.03 g) and iron powder (4.22 g), and the reaction mixture was stirred at 100° C. for 5 hours. The reaction mixture was filtered through a cotton plug, and then the filtrate was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (3.03 g) as a yellow solid.

1. extractionthe reaction mixture was extracted with ethyl acetate
2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationthe filtrate was concentrated under reduced pressure
5. stirringthe reaction mixture was stirred at 80° C. for 24 hours
6. additionTo the reaction mixture was added 2N-hydrochloric acid
7. extractionthe reaction mixture was extracted with ethyl acetate
8. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated under reduced pressure
11. dissolutionThe obtained residue was dissolved in tetrahydrofuran (20 mL)
12. additionTo the solution were added ammonium chloride (4.03 g) and iron powder (4.22 g)
13. stirringthe reaction mixture was stirred at 100° C. for 5 hours
14. filtrationThe reaction mixture was filtered through a cotton plug
15. extractionthe filtrate was extracted with ethyl acetate
16. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
17. filtrationfiltered
18. concentrationthe filtrate was concentrated under reduced pressure
19. customThe obtained residue was purified by silica gel column chromatography

ORD record

ord-c506a6b48815424bbba312a95cd10b44

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987473B2