Methanol → Methyl 4-iodopicolinate

HRID 901454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901454
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[CH3:16][O:9][C:8](=[O:10])[C:4]1[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][N:5]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 8182784-Iodopyridine-2-carboxylic acid

Produkt 1

HCID 22742038Methyl 4-iodopicolinateAusbeute 90 %

Versuchsvorschrift

To a solution of 4-iodopicolinic acid 11a (7.0 g, 18.6 mmol) in MeOH (70 mL) at 23° C. was added concentrated sulfuric acid (350 μL), and the reaction mixture was refluxed for 48 h. The reaction mixture was cooled to room temperature and concentrated to yield the desired product 4-iodopicolinic acid methyl ester 11b (4.4 g, 90%) as a yellow oil; 1H NMR (300 MHz, CDCl3) δ 8.52 (t, J=0.6, 1.5, 1), 8.40 (d, J=5.1, 1), 7.86-7.88 (dd, J=0.6, 5.1, 1), 4.02 (s, 3); MS (ESPOS): 263.9 [M+H];285.9 [M+Na].

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 48 h
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3202d3e84aea4b8d8ccb89a99cb20030
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361743B2

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