ChemicalBook CAS DataBase List Pyridine-3,5-dicarboxaldehyde

Pyridine-3,5-dicarboxaldehyde synthesis

6synthesis methods

Product Name:Pyridine-3,5-dicarboxaldehyde
CAS Number:6221-04-1
Molecular formula:C7H5NO2
Molecular Weight:135.12

3,5-Pyridinedicarboxamide, N3,N5-dimethoxy-N3,N5-dimethyl-

174496-55-0
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6221-04-1
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Yield:6221-04-1 54%

Reaction Conditions:

with diisobutylaluminium hydride in tetrahydrofuran;toluene at -78;Inert atmosphere;

Steps:

2.2 Synthesis of pyridine-3,5-dicarbaldehyde 3

Diamide 2 (1.00g, 3.95mmol) was dissolved in dry 8 THF (20mL) and cooled to-78°C under N₂ protection. A solution of 9 diisobutylaluminium hydride (8.30mL, 1M in 10 toluene) was added dropwise to the amide solution and the reaction was monitored by thin layer chromatography until no more starting material was observed. The reaction was carefully quenched using cold 11 water (0.2mL), 15% 12 NaOH (0.2mL) and then water (1.6mL), and was left stirring for 15min. The reaction was allowed to warm up to room temperature and 13 magnesium sulfate was added with stirring for another 15min. The mixture then passed through celite and washed with ethyl acetate (20mL x 3). The filtrate was dried under vacuum and purified over silica gel (ethyl acetate: hexane=1: 1), yielding a pale-yellow 14 solid (0.29g, 54%). M.p. 95-97°C; ¹H NMR (300MHz, CDCl₃): δ 8.56 (t, 1H, J=2.1Hz, NCHCCH), 9.25 (d, 2H, J=2.0Hz, NCHCCH), 10.2 (s, 2H, NCHCCHO); ¹³C NMR (75MHz, CDCl₃): δ 131.4 (s, 2C, CCHO), 136.0 (s, 1C, CCHC), 155.5 (s, 2C, NCH), 189.5 (s, 2C, CHO); HRMS (ESI) calcd for C₇H₆NO₂ [(M+H)⁺] 136.0399, found 136.0399.

References:

Yen Wong, Esther Hui;Jia, Yu-Xiang;Li, Yongxin;Pullarkat, Sumod A.;Leung, Pak-Hing [Journal of Organometallic Chemistry,2018,vol. 862,p. 22 - 27]