Dimethylformamide → HCID 53637785, compound

HRID 843989Notes

Reaction equation

HRID 843989 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.CN(C)C=O.[CH2:14]([O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1Cl)[CH3:15]>O>[CH2:14]([O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][C:19]=1[O:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH3:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 75103-PyridinemethanolHCID 2796614Ethyl chloronicotinate

Product 1

HCID 53637785HCID 53637785, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of Pyridin-3-yl-methanol (0.59 grams, 5.4 mmole) in dimethylformamide (20 ml) sodium hydride (0.259 grams, 6.5 mmole) was added and stirred for 30 minutes. 2-Chloro-nicotinic acid ethyl ester (1.0 grams, 5.4 mmole) was added via syringe and stirred at room temperature over night. The mixture was diluted with water (150 ml) and extracted by diethyl ether and ethyl acetate. The combined extracts were washed with 1N NaOH, water and brine, dried over Na2SO4, filtered, and concentrated to an oil (1.3 g). MW 258.28; MS (m/e) 259 (M++1).

Workup

  1. stirringstirred at room temperature over night
  2. extractionextracted by diethyl ether and ethyl acetate
  3. washThe combined extracts were washed with 1N NaOH, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil (1.3 g)

Sources & evidence

ORD record
ord-0ce986331d0e421c98cdf063c7beed42
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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