Nitrogen → HCID 23433481, compound

Temperature

0 °C

In a flame dried 100 mL rb flask equivuipped with a magnetic stir bar and a N2 gas inlet was dissolved (R/S)-4-ethyl-1,2,3,4-tetrahydro-7-methyloxyquinoline (21 mg, 109.9 μmol) in CH2Cl2 (4 mL). The solution was cooled to 0° C. and a 1.0M solution of BBr3 in CH2Cl2 (0.33 mL, 320 mmol, 2.75 equiv) was added slowly by syringe. The solution was warmed to rt and stirred under a blanket of N2 for 9 h. The reaction was quenched by addition of sat. NaHCO3 solution (5 mL), extracted with CH2Cl2 (3×25 mL), washed with brine (2×20 mL), dried (Na2SO4) and concentrated in vacuo to give 19 mg (99%) of the desired phenolic amine as a clear yellow oil. Data for (R/S)-4-ethyl-1,2,3,4-tetrahydro-7-hydroxyquinoline: 1H NMR (400 MHz, CDCl3) 6.85 (d, J=8.1, 1H), 6.11 (dd, J=2.4, 8.3, 1H), 5.98 (d, J=2.3, 1H), 3.25 (m, 2H), 2.57 (m, 1H), 1.85 (m, 1H), 1.76 (m, 1H), 1.67 (m, 1H), 1.51 (m, 1H), 0.940 (t, J=7.4, 3H).

1. customIn a flame dried 100 mL rb flask
2. customequivuipped with a magnetic stir bar and a N2 gas inlet
3. temperatureThe solution was warmed to rt
4. customThe reaction was quenched by addition of sat. NaHCO3 solution (5 mL)
5. extractionextracted with CH2Cl2 (3×25 mL)
6. washwashed with brine (2×20 mL)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated in vacuo

ORD record

ord-d33026ea61954e9786724a4ef22afea5

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05688810