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36053-96-0

7-METHYL-2,3-DIHYDROQUINOLIN-4(1H)-ONE synthesis

6synthesis methods
-

Yield:36053-96-0 46%

Reaction Conditions:

with trifluorormethanesulfonic acid in dichloromethane at 0 - 20; for 1 h;Inert atmosphere;

Steps:

50.3 Step 3: 7-methyl-2,3-dihydroquinolin-4(1H)-one (336-4)

To a solution of Compound 336-3 (5 g, 31.0 mmol) in DCM (100 mL) was added TfOH (9.3 g, 62.0 mmol) at 0°C under N2.The mixture was stirred at 20°C for 1hr. TLC indicated the reaction completed. The reaction mixture was quenched by poured into ice water (60 mL) and extracted with EtOAc (10 mL x 2). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue, which was purified by prep-HPLC to give Compound 336-7 (2.3 g, 14.3 mmol, 46% yield) as a yellow solid.1H NMR (400MHz, CHLOROFORM-d) d = 7.76- 7.74 (d, J=8 Hz, 1H), 6.58- 6.56 (d, J=8.4 Hz, 1H), 6.47 (s, 1H), 4.32 (s, 1H), 3.58 - 3.54 (m, 2H), 2.69- 2.66 (m, 2H), 2.26 (s, 3H).

References:

WO2021/3295,2021,A1 Location in patent:Paragraph 0547