Methanol → Methyl 4-iodopicolinate

HRID 1269000Notes

Reaction equation

HRID 1269000 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

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 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

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

Sources & evidence

ORD record
ord-7848b562abe64483afc47ce83bd5e299
Source dataset
uspto-grants-2007_04
Patent number
US07199106B2

Reaction notes

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