Dimethylformamide → HCID 18149883, compound

HRID 1874381Notes

Reaction equation

HRID 1874381 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:14][CH:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 18149883HCID 18149883, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3-hydroxybenzoate (8.14 g, 53.5 g), 2-chloro-5-nitropyridine (8.08 g, 51.0 mmol), potassium carbonate (11.1 g, 80.3 mmol) and N,N-dimethylformamide (100 mL) was stirred at 60° C. for 3 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (14.4 g, 98%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. filtrationthe residue was collected by filtration
  7. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-9534bd4f29584ce88cad3d5d98fb51d6
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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