6-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one → 6-Bromo-1,2,3,4-tetrahydro-4,4-dimethylquinoline

To 23.5 ml of 1.0 M (23.5 mmol) lithium aluminum hydride in THF, heated to reflux under nitrogen, was added to solution of 4.95 g (19.48 mmol) of 4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline (Compound 93) in 50 ml of dry THF and 100 ml of dry ether via a double-ended needle. The mixture was heated at reflux for 2 h and then cooled to room temperature. The reaction mixture was then quenched by the slow addition of 25 ml of water followed by 50 ml of 5% NaOH solution. The mixture was extracted with 2×25 ml of ether, the organic extracts were combined and washed successively with 25 ml each of water and saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 15% ethyl acetate in hexanes) to give the title compound as a brown oil. PMR (CDCl3): δ 1.27 (6H, s), 1.67-1.74 (2H, m), 3.23-3.32 (2H, m), 3.90 (1H, broad s), 6.33 (1H, d, J~8.4 Hz), 7.10 (1H, dd, J~8.4 Hz, 2.3 Hz), 7.25 (1H, d, J~2.3 Hz).

1. temperatureto reflux under nitrogen
2. temperatureThe mixture was heated
3. temperatureat reflux for 2 h
4. customThe reaction mixture was then quenched by the slow addition of 25 ml of water
5. extractionThe mixture was extracted with 2×25 ml of ether
6. washwashed successively with 25 ml each of water and saturated NaCl solution
7. dry with materialdried (MgSO4)
8. customThe solvent was removed in vacuo
9. customthe residue purified by flash chromatography (silica; 15% ethyl acetate in hexanes)

ORD record

ord-d6ef274af24b45559d2457755ce4ee72

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05248777