2-Hydroxy-4-(trifluoromethyl)quinoline Chemical Properties

Melting point:

>240°C

Boiling point:

284 ºC

Density 

1.391

Flash point:

126 ºC

storage temp. 

Sealed in dry,Room Temperature

form 

Solid

color 

White

InChI

InChI=1S/C10H6F3NO/c11-10(12,13)7-5-9(15)14-8-4-2-1-3-6(7)8/h1-5H,(H,14,15)

InChIKey

UUROBWTVZZNDFD-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C(C(F)(F)F)=CC1=O

CAS DataBase Reference

25199-84-2

Safety Information

Safety Statements 

24/25

HS Code 

29339900

2-Hydroxy-4-(trifluoromethyl)quinoline Usage And Synthesis

Uses

4-Trifluoromethyl-2-hydroxyquinoline has a wide range of applications in the pharmaceutical field and can be used as an intermediate for antibacterial, antiviral, anti-inflammatory and antitumor drugs.

Chemical Properties

White solid

Synthesis

4-Trifluoromethylquinolin-2(1H)-one was prepared by reacting aniline and ethyl-4,4,4-trifluoroacetoacetate stirred in toluene.
Experimental Procedure: In a 1 L round flask fitted with a reflux condenser a mixture of 25.60 g aniline, 50.0 g ethyl-4,4,4-trifluoroacetoacetate 300 ml toluene was heated to reflux in an oil bath at 130 °C. After 20 min 3 ml water was added and the mixture was heated at reflux for another 24 h. the reaction mixture was cooled to room temperature and concentrated under reduced pressure. A round flask with 200 mL H2SO4 was heated to 80°C and the crude oil from the step before was added in portions to the H2SO4 keeping the internal temperature below 90°C, total addition time was approximately 40 min. After addition was complete, the mixture was stirred at 80°C for 1 h, cooled and poured onto 400 g crushed ice. The resulting solids were filtered, washed with water, and dried under vacuum at 40°C to give 33.0 g (50%) product (2-Hydroxy-4-(trifluoromethyl)quinoline) as a colorless solid.

References

[1] Synthesis, 2003, # 13, p. 2005 - 2010
[2] Patent: WO2018/165385, 2018, A1. Location in patent: Paragraph 00362
[3] European Journal of Organic Chemistry, 2003, # 11, p. 2115 - 2121
[4] Patent: US2012/214803, 2012, A1. Location in patent: Page/Page column 172
[5] Patent: US2008/275057, 2008, A1. Location in patent: Page/Page column 86

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