5-Chloro-2-pyridinol → HCID 20326567, compound

HRID 372752Notes

Reaction equation

HRID 372752 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[Cl:9][CH2:10][C:11](=[O:14])[CH2:12]I>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Cl:9][CH2:10][C:11](=[O:14])[CH2:12][O:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 778895-Chloro-2-pyridinolHCID 234267321-Chloro-3-iodopropan-2-one

Product 1

HCID 20326567HCID 20326567, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
65 °C

Procedure

5-Chloro-2-pyridone (2.58 g.), silver carbonate (3.44 g.) and dry toluene (14 ml.) were stirred together under argon and heated to 65° C. for 20 minutes. A solution of 1-chloro-3-iodopropan-2-one (4 g.) in dry toluene (10 ml.) was added, and the mixture was stirred at 60°-65° C. for 3 hours, cooled, and filtered through "Hyflo" (trade mark) kieselguhr, washing the filter cake with toluene (15 ml.). The filtrate was evaporated to dryness, and the residue was purified by column chromatography on silica gel (100 g.), eluting with 10% v/v ethyl acetate in toluene. The first 130 ml. of eluate was discarded, and the next 60 ml. was collected, and evaporated to dryness to give 1-chloro-3-(5-chloropyrid-2-yloxy)propan-2-one, RF = 0.80 (50% v/v toluene in ethyl acetate).

Workup

  1. temperaturecooled
  2. filtrationfiltered through "Hyflo" (trade mark) kieselguhr
  3. washwashing the filter cake with toluene (15 ml.)
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by column chromatography on silica gel (100 g.)
  6. washeluting with 10% v/v ethyl acetate in toluene
  7. customwas collected
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-fc7940cf26314a918be70778512ea29f
Source dataset
uspto-grants-1978_05
Patent number
US04092323

Reaction notes

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