Ethanol → HCID 66782052, compound

HRID 1625970Notes

Reaction equation

HRID 1625970 reaction equation
Br[CH:2]([CH:7](Br)[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[C:11]2[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[C:3]([O:5][CH3:6])=[O:4].[OH-].[K+].[CH2:27](O)C>>[N:21]1[CH:22]=[CH:23][C:18]([C:11]2[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([C:7]#[C:2][C:3]([O:5][CH2:6][CH3:27])=[O:4])[CH:9]=3)[N:14]=[CH:13][CH:12]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 86625114HCID 86625114, compound

Product 1

HCID 66782052HCID 66782052, compoundYield 60%

Conditions

Temperature
95 °C

Procedure

A slurry of methyl 2,3-dibromo-3-[4-(4-pyridinyl)-6-quinolinyl]propanoate (4.20 g, 9.33 mmol) in ethanol (120 ml) was treated with solid potassium hydroxide pellets in one portion then heated at 95° C. for 2 hours. The reaction was cooled to room temperature then evaporated under reduced pressure. The resulting residue was diluted with ethanol (90 ml) and concentrated H2SO4 (3 ml) then heated at 95° C. for 3.5 hours. Cooled to room temperature then concentrated under reduced pressure. The resulting wet residue was taken into a minimum of water then made neutral with the addition of saturated aqueous NaHCO3 solution. This solution was extracted with EtOAc and the extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (EtOAc) to give the title compound (1.68 g, 60%) as a pale yellow solid. MS(ES)+ m/e 303 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthen evaporated under reduced pressure
  3. additionThe resulting residue was diluted with ethanol (90 ml) and concentrated H2SO4 (3 ml)
  4. temperaturethen heated at 95° C. for 3.5 hours
  5. temperatureCooled to room temperature
  6. concentrationthen concentrated under reduced pressure
  7. additionthen made neutral with the addition of saturated aqueous NaHCO3 solution
  8. extractionThis solution was extracted with EtOAc
  9. dry with materialthe extracts were dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customThe resulting residue was purified by silica gel chromatography (EtOAc)

Sources & evidence

ORD record
ord-21faa9e4a02c4a96a0aa01b63482c5a2
Source dataset
uspto-grants-2014_07
Patent number
US08785433B2

Reaction notes

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