ChemicalBook CAS DataBase List 7-Quinolinol, 1-ethyl-1,2-dihydro-2,2,4-trimethyl-

7-Quinolinol, 1-ethyl-1,2-dihydro-2,2,4-trimethyl- synthesis

7synthesis methods

Product Name:7-Quinolinol, 1-ethyl-1,2-dihydro-2,2,4-trimethyl-
CAS Number:150749-30-7
Molecular formula:C14H19NO
Molecular Weight:217.31

Quinoline, 1-ethyl-1,2-dihydro-7-methoxy-2,2,4-trimethyl-

150749-29-4
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7-Quinolinol, 1-ethyl-1,2-dihydro-2,2,4-trimethyl-

150749-30-7
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Yield: 85%

Reaction Conditions:

with hydrogen bromide in acetic acid

Steps:

3 N-ethyl-7-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline
EXAMPLE 3 N-ethyl-7-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline 20 g (0.086 mol) of N-ethyl-7-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline produced according to example 2 is heated to boiling point with 50 ml glacial acetic acid 50 ml hydrobromic acid (45%) for 6 hours. 200 ml water and 300 ml chloroform are added to the cooled reaction mixture. Subsequently the reaction mixture is neutralised with 30 % aqueous sodium hydroxide while cooling. The phases are separated and the aqueous phase is further extracted twice with 100 ml chloroform each time. The organic phases are pooled and dried over calcium chloride. After complete removal of the solvent in a rotary evaporator a light-green oil remains. Yield: 85%.

References:

Boehringer Mannheim GmbH US5750409, 1998, A

536-90-3 Synthesis