Chlorosuccinimide → 3-Chloroquinolin-4-ol

Temperature

60 °C

A mixture of 4-hydroxyquinoline (5.33 g, 36.7 mmol) in AcOH (184 mL) was treated with N-chlorosuccinimide (6.37 g, 47.7 mmol) and the yellow homogeneous mixture was stirred and heated at 60° C. After 3 h, the mixture was cooled to room temperature and concentrated in vacuo. Saturated aqueous NaHCO3 solution (300 mL) was added until pH became ˜8.5. The resulting solid was collected by filtration, washed with water (300 mL), and dried under high vacuum to give 3-chloroquinolin-4(1H)-one (A275-1) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.28 (1H, br. s.), 8.40 (1H, d, J=6.5 Hz), 8.15 (1H, dd, J=8.2, 1.4 Hz), 7.65-7.73 (1H, m), 7.58-7.63 (1H, m), 7.39 (1H, ddd, J=8.1, 6.9, 1.2 Hz); LCMS (ESI) m/z 180.1 (M+H)+.

1. temperaturethe mixture was cooled to room temperature
2. concentrationconcentrated in vacuo
3. additionSaturated aqueous NaHCO3 solution (300 mL) was added until pH
4. filtrationThe resulting solid was collected by filtration
5. washwashed with water (300 mL)
6. customdried under high vacuum

ORD record

ord-25e1c06bf91e4a8f8502664abc10d964

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2