Pyridine-2,5-dicarbaldehyde synthesis
- Product Name:Pyridine-2,5-dicarbaldehyde
- CAS Number:6221-01-8
- Molecular formula:C7H5NO2
- Molecular Weight:135.12
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Yield: 75%
Reaction Conditions:
with diisobutylaluminium hydride in dichloromethane;toluene at -78; for 1 h;
Steps:
1 4.3.1. 2,5-Pyridinedicarboxaldehyde (5)
To a stirred -78 °C solution of dimethyl pyridine-2,5-dicarboxylate (5.12 mmol) in 10 mL CH2Cl2 was added DIBAL (1.2 M in toluene, 10.70 mL, 1.28 mmol) dropwise.
The reaction was stirred at -78 °C for 1 h.
The reaction mixture was treated with saturated potassium sodium (+)-tartrate solution.
After extraction with CH2Cl2 (3 * 150 mL), the combined organic layers were washed with H2O (2 * 30 mL), brine (2 * 30 mL), and dried over MgSO4 prior to filtration and concentration under reduced pressure to yield the crude product.
The residue was purified by flash column chromatography to afford the product as a pale yellow powder.
Yield 75%, 1H NMR (400 MHz, CDCl3): δ 10.21 (s, 1H, CHO), 10.13 (s, 1H, CHO), 9.22 (s, 1H, ArH), 8.32 (d, J = 7.6 Hz, 1H, ArH), 8.09 (d, J = 8.0 Hz, 1H, ArH).
13C NMR (100 MHz, CDCl3): δ 192.31, 189.90, 155.52, 151.81, 137.28, 133.47, 121.69. MS calcd for C7H6NO2 (M + H)+, 136.03; found, 136.04.
References:
Fu, Chih-Wei;Hsieh, Yun-Jung;Chang, Tzu Ting;Chen, Chia-Ling;Yang, Cheng-Yu;Liao, Anne;Hsiao, Pei-Wen;Li, Wen-Shan [European Journal of Medicinal Chemistry,2015,vol. 104,p. 165 - 176] Location in patent:supporting information
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