ChemicalBook CAS DataBase List 4-HYDROXY-1-METHYL-2-QUINOLONE

4-HYDROXY-1-METHYL-2-QUINOLONE synthesis

9synthesis methods

Product Name:4-HYDROXY-1-METHYL-2-QUINOLONE
CAS Number:1677-46-9
Molecular formula:C10H9NO2
Molecular Weight:175.18

2(1H)-Quinolinone, 4-(acetyloxy)-1-methyl-

54350-10-6
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1677-46-9
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Yield: 100%

Reaction Conditions:

with sodium hydroxide in ethanol

Steps:

18 Synthesis of Derivative 12 of Hirtellanine Beta
N-methylaminobenzoic acid (500 mg, 3.3 lmmo 1)Was dissolved in 8 ml of acetic anhydride and acetic acid (1: 1, v / v)Of the mixed solution,The reaction solution was refluxed for 3 hours.The reaction was quenched by the slow addition of 10 ml of ice water and extracted three times with 15 ml each of ethyl acetate. The combined organic layers were washed once with 20 ml of saturated brine and the solvent was evaporated under reduced pressure. The resulting solid was dissolved in 20 ml of ethanol (0.1 eq) and stirred for 10 minutes. Ethanol was evaporated to dryness under reduced pressure and purified by column chromatography to give the intermediate 4-Hydroxy-l-methyl-lH-quinolin-2-one, which was further treated in the same manner as in Example 9 Method A The title compound derivative 12 (597 mg, yield 64%) was obtained.

References:

Basilea Pharmaceutica China Ltd;SHEN, ZHENGWU;ZHENG, SHUYAN;ZHANG, JINGHUA;SHOU, QINGYAO CN103319497, 2016, B Location in patent:Paragraph 0059; 0079