Methanol → Methyl 4-iodopicolinate

HRID 901454Notes

Reaction equation

[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

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 8182784-Iodopyridine-2-carboxylic acid

Product 1

HCID 22742038Methyl 4-iodopicolinateYield 90%

Procedure

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].

Workup

temperaturethe reaction mixture was refluxed for 48 h
concentrationconcentrated

Sources & evidence

ORD record: ord-3202d3e84aea4b8d8ccb89a99cb20030
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361743B2

Reaction notes

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