Dimethylformamide → HCID 14648776, compound

HRID 1073468Notes

Reaction equation

HRID 1073468 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CN(C)C=O.S(Cl)(Cl)=O.[CH2:20]([C:22](=[N:25]O)[CH2:23][CH3:24])[CH3:21]>C(Cl)(Cl)Cl.O.N1C=CC=CC=1>[OH:1][C:2]1[C:3]([C:8]([O:10][N:25]=[C:22]([CH2:23][CH3:24])[CH2:20][CH3:21])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 134013-Hydroxypicolinic AcidHCID 24386Thionyl ChlorideHCID 28017453-Pentanone oxime

Product 1

HCID 14648776HCID 14648776, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To 7.0 g of 3 hydroxypicolinic acid, 10 ml of N,N-dimethylformamide was added, and then 5.9 g of thionyl chloride was dropwise added thereto at a temperature of at most 10° C. The mixture was stirred at 0° C. for 30 minutes. To the reaction solution, 30 ml of chloroform was added, and the mixture was further stirred at 0° C. for 15 minutes. Then, a solution prepared by dissolving 5.0 g of diethyl ketone oxime in 50 ml of chloroform was dropwise added thereto at 0° C., and the mixture was stirred for 30 minutes. Then, 7.9 g of pyridine was dropwise added thereto. Then, the reaction solution was stirred at 0° C. for one hour and at room temperature for one day. The reaction solution was poured into water and extracted with ethyl acetate. Then, the extract was washed with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue thereby obtained was purified by silica gel column chromatography by using as a developing solvent a mixture of hexane/ethyl ether to obtain 6.5 g of the above identified compound as slightly yellow transparent viscous liquid.

Workup

  1. customat a temperature of at most 10° C
  2. stirringthe mixture was further stirred at 0° C. for 15 minutes
  3. customThen, a solution prepared
  4. additionwas dropwise added
  5. stirringat 0° C., and the mixture was stirred for 30 minutes
  6. stirringThen, the reaction solution was stirred at 0° C. for one hour and at room temperature for one day
  7. extractionextracted with ethyl acetate
  8. washThen, the extract was washed with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue thereby obtained
  12. customwas purified by silica gel column chromatography
  13. additiona mixture of hexane/ethyl ether
  14. customto obtain 6.5 g of the

Sources & evidence

ORD record
ord-fb5df819eefe43feb14a59e9c4dd9968
Source dataset
uspto-grants-1990_11
Patent number
US04969949

Reaction notes

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