ChemicalBook CAS DataBase List 2-(4-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID

2-(4-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID synthesis

4synthesis methods

Product Name:2-(4-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID
CAS Number:4364-02-7
Molecular formula:C17H13NO3
Molecular Weight:279.29

91-56-5 Synthesis

91-56-5
457 suppliers
$5.00/25g

100-06-1 Synthesis

100-06-1
591 suppliers
$18.19/25g

2-(4-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID

4364-02-7
48 suppliers
$15.00/5mg

Yield:4364-02-7 92%

Reaction Conditions:

Stage #1:indole-2,3-dione;1-(4-methoxyphenyl)ethanone with potassium hydroxide in ethanol;water at 80; for 20 h;Inert atmosphere;
Stage #2: with hydrogenchloride in water; pH=1Cooling with ice;

Steps:

1
1 H-lndole-2,3-dione (isatin; 4.000 g, 27.1864 mmol), 1-(3,4-dichloro- phenyl)-ethanone (4.695 g, 31.2644 mmol) and aqueous potassium hydroxide solution (85%; 81.5592 mmol) are dissolved in ethanol (99%; 30 ml) and the mixture is stirred at 80⁰C for 20 hrs under a nitrogen atmosphere. The resulting reaction mixture is evaporated, the residue is dissolved in water (30 ml) and the solution is washed with diethylether (2 x 20 ml). The aqueous phase is ice cooled, acidified to pH 1 with 37% HCI (-12 ml), and the red solid precipitated is filtered, washed with water and dried overnight (-7.6 g). This crude residue is purified by crystallization form diethylether and hexane (7.000, -92% yield).

References:

NEUROSEARCH A/S;NARDI, Antonio;CHRISTENSEN, Jeppe, Kejser;PETERS, Dan;DYHRING, Tino WO2010/20672, 2010, A1 Location in patent:Page/Page column 15

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123-11-5 Synthesis