2-QUINOLINYLMETHANOL Chemical Properties

Melting point:

64 °C

Boiling point:

205 °C(Press: 15 Torr)

Density 

1.218±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

14.29±0.10(Predicted)

color 

White to Off-White

CAS DataBase Reference

1780-17-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38-41-37/38

Safety Statements 

26-36/37/39-39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933491090

2-QUINOLINYLMETHANOL Usage And Synthesis

Uses

Intermediate in the preparation of aminopiperidines and related compounds as MCH receptor modulators useful in the treatment of metabolic, feeding and sexual disorders in humans.

Synthesis

General procedure for the synthesis of 2-hydroxymethylquinoline from methyl quinoline-2-carboxylate: a tetrahydrofuran (THF, 30 mL) solution of methyl quinoline-2-carboxylate (5 g, 26.8 mmol) was slowly added to a tetrahydrofuran (THF, 20 mL) solution containing sodium borohydride (NaBH4, 710 mg, 18.8 mmol) at room temperature. The reaction mixture was stirred at 35 °C for 30 min. Subsequently, methanol (2.5 mL), warm water (30 mL) and ethyl acetate (20 mL) were added sequentially at the same temperature. The organic layer was separated and washed with deionized water (2 x 30 mL). The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/methylcyclohexane=60/40) to give a white solid product in 73% yield. The melting point of the product was 135 °C (decomposition). Nuclear magnetic resonance hydrogen spectrum (1H NMR, 300 MHz, CDCl3) showed: δ 4.68 (1H, s, OH), 4.95 (2H, s, CH2), 7.31 (1H, m, aromatic CH), 7.55 (1H, m, aromatic CH), 7.71 (1H, m, aromatic CH), 7.81 (1H, m, aromatic CH), 8.10 (2H , m, aromatic CH). The nuclear magnetic resonance carbon spectrum (13C NMR, 75 MHz, CDCl3) showed: δ 64.25, 118.43, 126.35, 127.55, 127.69, 128.57, 129.81, 136.86, 146.72, 159.19. Calculated values for elemental analysis (C10H9NO): C, 75.45; H, 5.70 Measured values (C10H9NO): C, 75.45; H, 5.70; N, 8.80; measured values: C, 75.13; H, 5.56; N, 8.75.

References

[1] Organic Letters, 2005, vol. 7, # 17, p. 3609 - 3612
[2] Tetrahedron Letters, 2012, vol. 53, # 35, p. 4747 - 4750
[3] Tetrahedron, 2013, vol. 69, # 44, p. 9322 - 9328
[4] Tetrahedron Asymmetry, 2009, vol. 20, # 14, p. 1672 - 1682
[5] Journal of Organic Chemistry, 1953, vol. 18, p. 55,56

2-QUINOLINYLMETHANOL(1780-17-2)Related Product Information

• C-Quinolin-2-yl-methylamine dihydrochloride
• 4-Quinoline-carboxamide
• 2-Quinolinecarboxaldehyde
• 4-CYANOQUINOLINE
• 7-AMinoquinoline Hydrochloride
• 3-Quinolinecarboxaldehyde
• 3-Quinolinecarboxylic acid
• 6-Quinolinecarbaldehyde
• Quinoline-6-boronic acid
• QUINOLINE-6-SULFONYL CHLORIDE
• QUINAZOLIN-4-YLAMINE
• 8-Quinolinesulfonyl chloride
• methyl quinoline-3-carboxylate
• QUINOLIN-7-YLBORONIC ACID
• Quinoline-5-boronic acid
• Quinoline-5-carboxylic acid
• 2-QUINOLINYLMETHANOL
• 6-QUINOLINYLMETHANOL