Potassium Iodide → HCID 86651081, compound

HRID 1401140Notes

Reaction equation

HRID 1401140 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Cl)=[CH:6][N:5]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18]CC)=[O:17].[I-].[K+].[OH-].[Na+]>CN(C=O)C.O>[Cl:3][C:4]1[N:5]=[CH:6][C:7]([CH2:10][O:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=2)[C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 24522Ethyl 3-hydroxybenzoateHCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 86651081HCID 86651081, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

NaH (55% suspension in mineral oil, 1.2 g, 28 mmol) was slowly added to a suspension of 2-chloro-5-chloromethylpyridine (3.0 g, 19 mmol), ethyl 3-hydroxybenzoate (3.1 g, 19 mmol), and potassium iodide (600 mg, 3.7 mmol) in DMF (20 ml). After stirring for 2 days at 20° C., water (10 ml) and NaOH (32.5%, 2 ml) was added. The dark mixture was stirred at 80° C. overnight, wereupon it was concentrated in vacuo. The residue was purified by preparative LC-MS to give 0.80 g of the title compound. LC-MS (m/z): 264 (M+1).

Workup

  1. stirringThe dark mixture was stirred at 80° C. overnight, wereupon it
  2. concentrationwas concentrated in vacuo
  3. customThe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-ff56d50b12fb4ed08ae2b0693f82670d
Source dataset
uspto-grants-2014_12
Patent number
US08907096B2

Reaction notes

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