Phosphorus oxychloride → HCID 86694549, compound

Temperature

105 °C

To a single-neck reaction flask (100 ml) were added 4-hydroxy-6-nitro-7-(tetrahydrofuran-3-yl-oxy)quinoline-3-carbonitrile (1.8 g, 3 mmol) and POCl3 (10 mL) under argon atmosphere. The mixture was warmed to the temperature of 105° C. The reaction mixture was stirred for 2.5 hr. Then the reaction was stopped. The resultant mixture was rotary-evaporated to dryness. DCM (20 mL) was added to dissolve the resultant mixture. The solution was poured into a cooled mixture solution of DCM (200 mL) and saturated K2CO3 solution (60 mL). The resultant mixture was stirred for 10 min. The solution was extracted and the aqueous layer was discarded. The DCM layer was washed with water (150 mL) and staturated NaCl solution (150 mL), successively. The resultant substance was dried over MgSO4 for half-hour, filtered, rotary-evaporated to dryness, and dried in vacuo to give a yellow solid (1.771 g). Yield: 92.7%.

1. customThe resultant mixture was rotary-evaporated to dryness
2. additionDCM (20 mL) was added
3. dissolutionto dissolve the resultant mixture
4. additionThe solution was poured into a cooled mixture solution of DCM (200 mL) and saturated K2CO3 solution (60 mL)
5. stirringThe resultant mixture was stirred for 10 min
6. extractionThe solution was extracted
7. washThe DCM layer was washed with water (150 mL) and staturated NaCl solution (150 mL)
8. dry with materialThe resultant substance was dried over MgSO4 for half-hour
9. filtrationfiltered
10. customrotary-evaporated to dryness
11. customdried in vacuo

ORD record

ord-9a8628dcac0247c9b5e9ea14ec2c6a66

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187458B2