Yield:120689-98-7 74%

Reaction Conditions:

with aluminum (III) chloride in 1,2-dichloro-benzene at 50 - 70;Heating / reflux;

Steps:

21B B. 4,4,8-trimethyl-3,4-dihydro-1H-quinolin-2-one

To a solution of 3-methyl-but-2-enoic-acid o-tolylamide (7.27g, 38.41 mmole, 1eq) in 1,2-dichlorobenzene (50 ml) was added aluminum chloride (AlCl3) (30.73 g, 230.49 mmole, 6 eq) and the whole heated to 50-70 C. As the reaction reached about 50 C vigorous HCI (g) was released. After the HCl evolution appeared to cease, the reaction was allowed to continue for an additional 10 min before cooling. The reaction was cooled and poured into cold H2O. The heterogeneous mix was extracted with CH2Cl2 (3 x 100 ml), dried (MgSO4) and concentrated to an orange oil which was purified by MPLC (30 % EA/Hex) to give the above titled compound (5.357 g, 28.31 mmole, 74 % yield). 1H NMR (400 MHz, CDCl3) δ 8.43 (s, 1H), 7.16 (d, J = 7.5Hz, 1H), 7.04 (d, J = 7.5Hz, 1H), 6.96 (t, J = 7.5Hz, 1H), 2.48 (s, 2H), 2.30 (s, 3H), 1.32 (s, 6H)

References:

WO2004/26864,2004,A1 Location in patent:Page 59