8-FLUORO-3,4-DIHYDRO-1H QUINOLIN-2-ONE synthesis
- Product Name:8-FLUORO-3,4-DIHYDRO-1H QUINOLIN-2-ONE
- CAS Number:143268-79-5
- Molecular formula:C9H8FNO
- Molecular Weight:165.16
349097-66-1
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143268-79-5
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Yield:143268-79-5 88%
Reaction Conditions:
aluminum (III) chloride at 160; for 1.5 h;
Steps:
41
8-Fluoro-3,4-dihydroquinolin-2(1H)-one (4) 3-Chloro-N-(2-fluorophenyl)propanamide (3.3 g, 16.4 mmol) and aluminum trichloride (10.9 g, 81.8 mmol) were combined in a RB flask with a stirbar and purged with argon. The mixture of the two solids was heated to 160° C. to form a melt, which was stirred for 1.5 h. The mixture was then removed from the heating bath and when it had cooled to below 100° C., was quenched by careful addition of water. The resulting mixture was cooled to room temperature, neutralized with NaOH, and extracted with dichloromethane (3*). The combined organics were dried, filtered and evaporated, then chromatographed on silica gel using 20% EtOAc in hexanes, giving the desired product. 1H NMR showed some impurities. Yield: 2.35 g, 88%. 1H NMR (CDCl3) δ 2.66 (t, 2H, J=7.6 Hz), 3.01 (t, 2H, J=7.6 Hz), 6.96 (m, 3H), 8.11 (brs, 1H).
References:
US2008/234237,2008,A1 Location in patent:Page/Page column 74
348-54-9
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143268-79-5
48 suppliers
$45.00/10mg