2-(2-HYDROXYETHYL)QUINOLINE Chemical Properties

Melting point:

103-104℃

Boiling point:

303.86°C (rough estimate)

Density 

1.177

refractive index 

1.4950 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

14.84±0.10(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C11H11NO/c13-8-7-10-6-5-9-3-1-2-4-11(9)12-10/h1-6,13H,7-8H2

InChIKey

VPDAGUVEZGEHJJ-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C=CC=1CCO

EPA Substance Registry System

2-Quinolineethanol (1011-50-3)

Safety Information

HS Code 

2933499090

2-(2-HYDROXYETHYL)QUINOLINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-(2-hydroxymethyl)quinoline from ethyl 2-quinolineacetate: ethyl 2-quinolineacetate (8.6 g, 42.8 mmol) was dissolved in ether (400 mL) and cooled to -78 °C. At -78 °C, lithium aluminum hydride (1.63 g, 42.8 mmol) was added in batches. After maintaining -78 °C for 2 hours of stirring, the temperature was slowly increased to 0 °C and stirring was continued at 0 °C for 4 hours, followed by stirring at room temperature overnight. Upon completion of the reaction, the mixture was cooled to 0 °C and a small amount of methanol was added to quench unreacted lithium aluminum hydride, followed by sodium sulfate decahydrate (43 g). After stirring for 1 h at room temperature, the reaction mixture was filtered, the solid residue was washed with chloroform, and the filtrates were combined and concentrated. Purification by silica gel column chromatography (eluent ratio 2:1 ethyl acetate-hexane) afforded 0.46 g (53% yield) of 2-(2-hydroxymethyl)quinoline. The product was confirmed by 13C NMR (101 MHz, chloroform-D) with chemical shifts of δ 161.53, 147.23, 137.04, 130.01, 128.74, 127.79, 127.03, 126.39, 122.09, 61.60, 39.52 ppm; mass spectrometry (AP/CI) showed the molecular ion peak m/z 174.2 (M + H)+.

References

[1] Patent: WO2008/20302, 2008, A2. Location in patent: Page/Page column 26
[2] Patent: WO2014/140184, 2014, A1. Location in patent: Page/Page column 71-72
[3] Monatshefte fuer Chemie, 1952, vol. 83, p. 915,922

2-(2-HYDROXYETHYL)QUINOLINE(1011-50-3)Related Product Information

• 2-(2-HYDROXYETHYL)QUINOLINE
• AMINO-QUINOLIN-2-YL-ACETIC ACID
• DIETHYL 2-(8-HYDROXYQUINOLIN-2-YL)MALONATE
• 2-[2-((4,6-DIMETHYLPYRIMIDIN-2-YL)OXY)-2-(4-(TRIFLUOROMETHYL)PHENYL)ETHYL]QUINOLINE
• 2-[2-((4,6-DIMETHYLPYRIMIDIN-2-YL)OXY)-2-PHENYLETHYL]QUINOLINE
• 2-[2-((4,6-DIMETHOXYPYRIMIDIN-2-YL)OXY)-2-(3-(TRIFLUOROMETHYL)PHENYL)ETHYL]QUINOLINE
• 1,1,1-TRICHLORO-3-QUINOLIN-2-YLPROPAN-2-OL
• 2-[2-((4,6-DIMETHYLPYRIMIDIN-2-YL)OXY)-2-(4-METHOXYPHENYL)ETHYL]QUINOLINE
• Ethyl alpha-cyano-4-((diethylamino)carbonyl)-2-quinolineacetate
• Ethyl alpha-cyano-4-(4-morpholinylcarbonyl)-2-quinolineacetate
• 2-[2-((4,6-DIMETHOXYPYRIMIDIN-2-YL)OXY)-2-PHENYLETHYL]QUINOLINE
• RARECHEM AK HZ 0054
• 2-[2-((4,6-DIMETHOXYPYRIMIDIN-2-YL)OXY)-2-(4-METHOXYPHENYL)ETHYL]QUINOLINE
• 2-[2-((4,6-DIMETHOXYPYRIMIDIN-2-YL)OXY)-2-(4-(TRIFLUOROMETHYL)PHENYL)ETHYL]QUINOLINE
• 2-[2-((4,6-DIMETHYLPYRIMIDIN-2-YL)OXY)-2-(3-(TRIFLUOROMETHYL)PHENYL)ETHYL]QUINOLINE
• TRANS-5,6-DIHYDROXY-5,6-DIHYDRODIBENZ(A,J)ACRIDINE
• Ethyl alpha-cyano-4-(1-piperidinylcarbonyl)-2-quinolineacetate
• Ethyl 4-((butylamino)carbonyl)-alpha-cyano-2-quinolineacetate