613-21-8

Usage

Uses

2-Methylquinolin-6-ol can be used as agricultural and horticultural fungicides.

InChI:InChI=1/C10H9NO/c1-7-2-3-8-6-9(12)4-5-10(8)11-7/h2-6,12H,1H3

Upstream product

• 58484-75-6 (E)-4-(4-hydroxyphenyl)butan-2-one oxime 

Downstream Products

• 874949-69-6 C₅₃H₄₅NO₁₃ 
• 176751-71-6 methyl 4-(6-quinaldinyloxy)-3-methylsulfonyl-benzoate 
• 918946-07-3 6-(2,6-dibromo-4-nitrophenoxy)-2-methylquinoline 
• 1221541-85-0 6-(tert-butyldiphenylsilyloxy)-2-methylquinoline 
• 1420180-96-6 6-(2,4-dinitrophenoxy)-2-methylquinoline 
• 1620101-26-9 6-(2-ethoxy-2-oxoethoxy)-2-methyl-8-(4-methylphenylsulfonamido)quinoline N-oxide 
• 181530-09-6 ethyl [(2-methyl-8-p-toluenesulfonylaminoquinolin-6-yloxy)acetate] 
• 91875-31-9 2-methyl-6-phenylquinoline 
• 6628-28-0 6-ethoxy-2-methyl-quinoline 

Relevant academic research and scientific papers

SN2 substitution on sp2 nitrogen of protonated oxime

Theoretical studies on intramolecular nucleophilic displacement of the prolonated oxime oxygen willi an aryl ring revealed that the substitution reaction on the sp2 nitrogen atom is a low energy process. This seemingly anomalous substitution is due to the low-lying σ*-orbital of the O-protonated oxime. The theoretical conclusion received experimental support.

Regioselective synthesis of quinolin-8-ols and 1,2,3,4- tetrahydroquinolin-8-ols by the cyclization of 2-(3-hydroxyphenyl)ethyl ketone 0-2,4-dinitrophenyloximes

Cyclization of 2-(3-hydroxyphenyl)ethyl ketone 0-2,4- dinitrophenyloximes proceeds on the oxime nitrogen atom by the treatment with NaH and then with 2,3-dichloro-5,6-dicyano-p-benzoquinone and acetic acid to yield quinolin-8-ols regioselectively. The reaction in the presence of Na[BH3(CN)] affords 1,2,3,4-tetrahydroquinolin-8-ols. The present cyclization proceeds via alkylideneaminyl radical intermediates generated by the single electron transfer between 3-hydroxyphenyl and 2,4-dinitrophenyl moieties.

Synthesis of 8-hydroxyquinolines by the cyclization of m-hydroxyphenethyl ketone O-2,4-dinitrophenyloximes

8-Hydroxyquinolines are synthesized from O-2,4-dinitrophenyloximes of m-hydroxyphenethyl ketones by the treatment with sodium hydride, and then with 2,3-dichloro4,5-dicyano-p-benzoquinone (DDQ).