Nicotinic Acid → 4-Formyl-2-methoxyphenyl pyridine-3-carboxylate

HRID 44447

Reaktionsgleichung

Reaktionsgleichung von HRID 44447
[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([C:7]([OH:9])=[O:8])[CH:2]=1.[O:10]=[CH:11][C:12]1[CH:20]=[CH:19][C:17](O)=[C:14]([O:15][CH3:16])[CH:13]=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>ClCCl.O>[CH:11]([C:12]1[CH:20]=[CH:19][C:17]([O:8][C:7](=[O:9])[C:3]2[CH:2]=[CH:1][CH:6]=[N:5][CH:4]=2)=[C:14]([O:15][CH3:16])[CH:13]=1)=[O:10]

Komponenten

7

Edukt 4

HCID 938Nicotinic AcidHCID 1183VanillinHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 8897804-Formyl-2-methoxyphenyl pyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Niacin 1 (1.6 g, 13.1 mmol) in dichloromethane (10 mL) was added Vanillin 8 (2 g, 13.1 mmol), N-methyl morpholine (4.3 mL, 39 mmol) and EDCI.HCl (5 g, 26.2 mmol). The resulting mixture was stirred at ambient temp for 3 h. It was then diluted with water, extracted with dichloromethane, and the organic layer dried over anhydrous sodium sulfate and concentrated. The crude product thus obtained was then chromatographed using over a column of silica gel using petroleum ether:ethyl acetate (1:1) to afford the title compound as a off white solid (300 mg, 9%, mp (° C.): 92-94) 1H NMR (300 MHz, DMSO-D6): 10.02 (s, 1H), 9.25 (d, J=2 Hz, 1H), 8.93 (dd, J=5 & 1.5 Hz, 1H), 8.48 (dt, J=1.8 Hz & 8 Hz, 1H), 7.67 (m, 3H), 7.57 (d, J=8 Hz, 1H), 3.87 (s, 3H)); LCMS (m/z): 257.7 (M+1); HPLC: tRet: 6.486 (98.9%).

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialthe organic layer dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product thus obtained
  5. customwas then chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-27a5bf611e6f4369a2f8f23bcfff16de
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541435B2

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