Potassium Hydroxide → HCID 57431526, compound

HRID 2041945Notes

Reaction equation

HRID 2041945 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12]([O:14]C)=[O:13])=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO.O>[N:1]1([C:6]2[N:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[C:8]([C:16]([F:19])([F:17])[F:18])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68430391HCID 68430391, compound

Product 1

HCID 57431526HCID 57431526, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2.5 g (9.12 mmol) of methyl 6-(pyrrolidin-1-yl)-4-(trifluoromethyl)pyridine-3-carboxylate, obtained in step 11.1, and of 0.76 g (13.67 mmol) of potassium hydroxide in 50 ml of methanol and 2 ml of water is stirred for 24 hours at 20° C. The mixture is subsequently concentrated under reduced pressure. 100 ml of water are subsequently added and the solution is washed with 100 ml of dichloromethane and then acidified to pH 4 by the addition of concentrated hydrochloric acid. A precipitate is recovered by filtration and is washed with 50 ml of water. After drying under reduced pressure, 2.2 g of the expected compound are isolated.

Workup

  1. customobtained in step 11.1
  2. concentrationThe mixture is subsequently concentrated under reduced pressure
  3. addition100 ml of water are subsequently added
  4. washthe solution is washed with 100 ml of dichloromethane
  5. additionacidified to pH 4 by the addition of concentrated hydrochloric acid
  6. filtrationA precipitate is recovered by filtration
  7. washis washed with 50 ml of water
  8. dry with materialAfter drying under reduced pressure, 2.2 g of the expected compound
  9. customare isolated

Sources & evidence

ORD record
ord-894912d415ef42a8bc46424d232b8153
Source dataset
uspto-grants-2013_11
Patent number
US08586573B2

Reaction notes

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