ChemicalBook CAS DataBase List 6-CHLORO-4-HYDROXY-2-METHYLQUINOLINE

6-CHLORO-4-HYDROXY-2-METHYLQUINOLINE synthesis

8synthesis methods

Product Name:6-CHLORO-4-HYDROXY-2-METHYLQUINOLINE
CAS Number:15644-86-7
Molecular formula:C10H8ClNO
Molecular Weight:193.63

Butanoic acid, 3-[(4-chlorophenyl)imino]-, ethyl ester

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Yield:15644-86-7 75%

Reaction Conditions:

in diphenylether at 240; for 1 h;Dean-Stark;

Steps:

2.2. General Method for Synthesis of 4-hydroxy-2-methylquinoline

General procedure: Aniline (2.28 mL, 25 mmol), ethyl acetoacetate (6.37 mL,50 mmol), benzene (25 mL) and glacial acetic acid (1 mL,catalytic amount) were made to react in a round bottomedflask equipped with DeanStark apparatus fitted with a refluxcondenser at 100°C till no more water left for separation out. Benzene was distilled under the reduced pressure and theresulting imine intermediate 4a was obtained in 98% yield(5.02 g, 24.5 mmol). The intermediate 4a was then used inthe next step without further purification. 4a was added rapidlyto pre-stirred diphenyl ether (30 mL) in a roundbottomedflask equipped with a Dean-Stark trap and maintainedat reflux till ethanol was separated. The reaction mixturewas cooled to ambient temperature to allow precipitation.The solid was filtered off and washed with hexane andacetone to yield 4-hydroxy-2-methylquinoline (5a, 2.92 g,18.36 mmol) (Scheme 1) in 75% yield.

References:

Mahajan, Shivani;Gupta, Shiv;Jariwala, Nisha;Bhadane, Deepali;Bhutani, Late K.K.;Kulkarni, Smita;Singh, Inder Pal [Letters in drug design and discovery,2018,vol. 15,# 9,p. 937 - 944]

141-97-9 Synthesis