Peracetic Acid → 3-Hydroxyquinoline

Temperature

-78 °C

3-Bromoquinoline (5.0 g, 24.03 mmoL) was dissolved in anhydrous ether and cooled to −78° C. It was then treated with n-butyllithium (10.57 mL, 26.43 mmoL, 2.5M in hexanes) by slow addition over 30 min. The reaction was stirred at −78° C. for 30 min then it was treated with trimethylborate (2.50 g, 24.03 mmoL) by slow addition over 10-15 min. The reaction was then allowed to stir at 0° C. for 45 min then at room temperature for 15 min. The reaction was then cooled back to −78° C. and treated with peracetic acid (5.49 g, 26.44 mmoL) and stirred at room temperature for 20 hr. The reaction was diluted with H2O (40 mL) and solid sodium bisulfite was added until the peroxides were destroyed as indicated with peroxide test strips. The layers were separated and the aqueous layer extracted with ethyl acetate (2×50 mL). The organic layer was concentrated in vacuo and the residue was azeodried with toluene (4×50 mL). The residue was triturated with toluene and the solids were collected by vacuum filtration to give 1.43 g (41%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.29 (s, 1H) 8.58 (d, J=2.57 Hz, 1H) 7.85-7.95 (m, 1H) 7.72-7.83 (m, 1H) 7.40-7.57 (m, 3H). MS m/z (DCI) 146.0 (M+H)+.

1. stirringto stir at 0° C. for 45 min
2. waitat room temperature for 15 min
3. temperatureThe reaction was then cooled back to −78° C.
4. stirringstirred at room temperature for 20 hr
5. customwere destroyed
6. customThe layers were separated
7. extractionthe aqueous layer extracted with ethyl acetate (2×50 mL)
8. concentrationThe organic layer was concentrated in vacuo
9. customThe residue was triturated with toluene
10. filtrationthe solids were collected by vacuum filtration

ORD record

ord-24031d34eb47437593a8dca07f16b80a

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207350B2