(2-Phenylquinolin-4-yl)methanol synthesis
- Product Name:(2-Phenylquinolin-4-yl)methanol
- CAS Number:29268-33-5
- Molecular formula:C16H13NO
- Molecular Weight:235.28
4546-48-9
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Yield:29268-33-5 100%
Reaction Conditions:
with diisobutylaluminium hydride in dichloromethane;toluene at -78 - 20;Inert atmosphere;
Steps:
20 4-hydroxymethyl-2-phenyl-quinoline
To a solution of 2.1 g (8 mmol) of methyl 2-phenyl-quinoline-4-carboxylate in 50 ml of dichloromethane was added at -78°C under nitrogen, 12 ml (12 mmol) of Diisobutylaluminium hydride 1M in toluene and the mixture was stirred for one night at room temperature. After cooling the mixture, methanol was added at 0°C, and then 15 g (7 eq.) of potassium sodium tartrate dissolved in 50 ml of water. The mixture was stirred for 1 h at room temperature and extracted with dichloromethane. The organic layer was dried over MgS04, filtered and concentrated to give 2.01 g of yellow oil (quantitative yield) corresponding to 4-hydroxymethyl-2-phenyl-quinoline. HPLC-MS: conditions D: tr = 4.39 min, (ES+) C16H13NO requires 235; found 236 [M + H], purity 95 %. 1H NMR (300 MHz, CDC13).
References:
WO2014/147611,2014,A1 Location in patent:Page/Page column 101; 102
100-52-7
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62-53-3
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132-60-5
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