1-Chloroethyl chloroformate → HCID 18462043, compound

2-Benzyl-10-chloro-1,2,3,4-tetrahydro-benzo[b][1,6]-naphthyridine (1.54 g, 5 mmol) was dissolved in methylene chloride, followed by adding thereto 1-chloroethyl chloroformate (0.81 ml, 7.5 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and methanol (20 ml) was added to the residue, and the resulting mixture was heated under reflux at 80° C. for 1 hour. The reaction mixture was concentrated and a 1N-aqueous potassium hydroxide solution was added thereto, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by suspension in diethyl ether/hexane to obtain the desired compound (656.4 mg, 60%) as a light-yellowish-white substance.

1. additionby adding
2. concentrationThe reaction mixture was concentrated
3. additionmethanol (20 ml) was added to the residue
4. temperaturethe resulting mixture was heated
5. temperatureunder reflux at 80° C. for 1 hour
6. concentrationThe reaction mixture was concentrated
7. additiona 1N-aqueous potassium hydroxide solution was added
8. extractionfollowed by extraction with methylene chloride
9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure
11. customthe resulting residue was purified by suspension in diethyl ether/hexane

ORD record

ord-abce8973437745ab9a4843b94b4337d0

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06294547B1