| Identification | More | [Name]
2-QUINOLINYLMETHANOL | [CAS]
1780-17-2 | [Synonyms]
2-HYDROXYMETHYLQUINOLINE
2-QUINOLINEMETHANOL
2-QUINOLINYLMETHANOL
QUINOLIN-2-YLMETHANOL
RARECHEM AK ML 0556
2-quinolylmethanol
2-QUINOLINONE
2-Quinolineylmethanol
α-Quinaldinol | [EINECS(EC#)]
217-225-7 | [Molecular Formula]
C10H9NO | [MDL Number]
MFCD00086626 | [Molecular Weight]
159.18 | [MOL File]
1780-17-2.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
2933491090 |
| Hazard Information | Back Directory | [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 |
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