Potassium Hydroxide → HCID 68897891, compound

HRID 1437154Notes

Reaction equation

HRID 1437154 reaction equation
C(OC([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8](C2CCN(C(OCC)=O)CC2)=[CH:7]1)=O)C.[OH-].[K+]>C(O)(C)C>[N:11]1([C:8]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:6][CH:7]=2)[CH2:12][CH2:13][CH2:14][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68895547HCID 68895547, compound

Product 1

HCID 68897891HCID 68897891, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

14.67 g (42.0 mmol) of 3-(1-ethoxycarbonyl-piperidin-4-yl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid ethyl ester were added to a solution of 40.32 g (720 mmol) of potassium hydroxide in 630 ml of isopropanol. The mixture was refluxed for 20 hours. The solvent was distilled off and cold water was added. This solution was acidified with concentrated hydrochloric acid and then basified with 8 N aqueous sodium hydroxide solution. This aqueous solution was extracted twice with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure affording 4.66 g (48% of yield) of the expected product as an oil.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. distillationThe solvent was distilled off
  3. additioncold water was added
  4. extractionThis aqueous solution was extracted twice with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customaffording

Sources & evidence

ORD record
ord-01c39af063d0439a924820a2591ca6d2
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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