6-methoxy-4-(trifluoromethyl)-1H-quinolin-2-one synthesis
- Product Name:6-methoxy-4-(trifluoromethyl)-1H-quinolin-2-one
- CAS Number:328956-13-4
- Molecular formula:C11H8F3NO2
- Molecular Weight:243.18
Yield:328956-13-4 70%
Reaction Conditions:
Stage #1: 4-methoxy-aniline;ethyl 4,4,4-trifluoroacetoacetate at 150; for 12 h;Knorr Quinoline synthesis;
Stage #2: with sulfuric acid at 95; for 6 h;Knorr Quinoline synthesis;
Steps:
5.1.8. Synthesis of methoxy quinolin-2(1H)-ones (28-29)
General procedure: Anisidine (2 g, 16.0 mmol) was added dropwise to substituted ethyl acetoacetate (3 mL, 16.0 mmol), the mixture was refluxed for 12 h. The mixture was then cooled and poured on sodium carbonate solution. The compound was then extracted with 50 ml ethyl acetate and the solvent was evaporated. 70% Sulphuric acid (5 mL) was added to it and the solution was heated at 95 °C for 6 h. It was then poured on crushed ice (100 g) and the precipitate was filtered and washed with water and ether. The crude product so obtained was purified by column chromatography.
References:
Kathuria, Abha;Priya, Nivedita;Chand, Karam;Singh, Prabhjot;Gupta, Anjali;Jalal, Sarah;Gupta, Shilpi;Raj, Hanumantharao G.;Sharma, Sunil K. [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 4,p. 1624 - 1638] Location in patent:experimental part
