Oxygen → HCID 18466701, compound

5,8-Dimethyl-2-(2-furyl)-5,6,7,8-tetrahydroquinoline (3 g) was dissolved in 100 ml of methanol. Ozone generated from oxygen at -78° C. was introduced into the obtained solution for 10 minutes. The resulting system was saturated with nitrogen gas, followed by the addition of 7 ml of dimethyl sulfide. The temperature of the mixture was raised to room temperature and the resulting reaction mixture was concentrated to give about 3 g of a crude product. This crude product containing a carboxylic acid was dissolved in 10 ml of DMF, followed by the addition of 1 ml of methyl iodide and 3.6 g of K2CO3. The obtained mixture was stirred at room temperature for one hour, followed by the addition of 30 ml of water. The obtained mixture was extracted with ethyl acetate (50 ml×2) and the organic phase was washed with a saturated aqueous solution of common salt, dried over MgSO4 and concentrated. The obtained mixture was purified by column chromatography to give 1.6 g of the objective compound.

1. additionwas introduced into the obtained solution for 10 minutes
2. customthe resulting reaction mixture
3. concentrationwas concentrated
4. customto give about 3 g of a crude product
5. extractionThe obtained mixture was extracted with ethyl acetate (50 ml×2)
6. washthe organic phase was washed with a saturated aqueous solution of common salt
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe obtained mixture was purified by column chromatography

ORD record

ord-945a7d86049441189b5642cb6b6a1033

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133283