ChemicalBook CAS DataBase List 5,6-Dimethoxynicotinaldehyde

5,6-Dimethoxynicotinaldehyde synthesis

5synthesis methods

Product Name:5,6-Dimethoxynicotinaldehyde
CAS Number:52605-99-9
Molecular formula:C8H9NO3
Molecular Weight:167.16

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Yield:-

Reaction Conditions:

Stage #1: 2,3-dimethoxy-5-vinylpyridinewith osmium(VIII) oxide;4-methylmorpholine N-oxide in tetrahydrofuran;water at 25; for 0.5 h;
Stage #2: with sodium periodate in tetrahydrofuran;water at 25; for 12 h;

Steps:

5.2 Step 2: 5, 6-Dimethoxynicotinaldehyde

NMO (3.83g, 32.7mmol) and 0s0₄ (0.040M in 0, 42mL, l.7mmol) were added to a mixture of 2,3-dimethoxy-5-vinylpyridine (2.70g, l6.3mmol) in THF (60mL) and H2O (l5mL). The reaction mixture was stirred at RT for 30 min. NaI0₄ (6.99g, 32.7mmol) was added, and the reaction mixture was stirred at RT for 12 hours. The reaction mixture was diluted with H2O (50mL) and EtOAc (50mL). The reaction mixture was extracted with EtOAc (3x50 mL). The organic layers were combined, washed with brine (50mL), dried over MgS0₄, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting EtOAc in PE) to afford 5,6-dimethoxynicotinaldehyde. LCMS (CxHioNOri (ES, m/z): 168 [M+H]⁺. ^XH NMR (400MHz, CDCf-ri) 5=9.94 (s, 1H), 8.21 (d, =l.8Hz, 1H), 7.48 (d, J=l.8Hz, 1H), 4.12 (s, 3H), 3.94 (s, 3H).

References:

WO2019/195063,2019,A1 Location in patent:Page/Page column 45; 54-55

52605-96-6 Synthesis