Water → HCID 53884565, compound

HRID 843981Notes

Reaction equation

HRID 843981 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1Cl)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[N:24][CH:25]=1.O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:26][C:22]1[CH:23]=[N:24][CH:25]=[C:20]([Cl:19])[CH:21]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5823053-Hydroxy-5-chloropyridineHCID 2796614Ethyl chloronicotinate

Product 1

HCID 53884565HCID 53884565, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-Chloro-nicotinic acid ethyl ester (2.07 grams, 11.2 mmole), Cesium carbonate (7.27 grams, 22.3 mmole) and 5-chloro-3-pyridinol (1.45 grams, 11.2 mmole) in dry dimethylformamide (40 ml) was stirred at 90° C. overnight. The suspension was cooled to room temperature, poured into water and extracted with diethyl ether. The combined organics were washed with water and brine, dried over MgSO4, and concentrated to a tan solid. Recrystalization from hexane gave a yellow solid (1.0 g). M.P. 65-69° C.; Anal. calcd. for C13H11ClN2O3: C, 56.03; H, 3.98; N, 10.05. Found: C, 56.14; H, 4.04; N, 10.16.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organics were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to a tan solid
  5. customRecrystalization from hexane

Sources & evidence

ORD record
ord-1b4e933c0cfe4a5188333c36216c9552
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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