Sodium Hydroxide → HCID 21904722, compound

HRID 1394094Notes

Reaction equation

HRID 1394094 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:4]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]([O:17]C)=[O:16])[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>C1COCC1.O>[F:19][C:2]([F:1])([F:20])[C:3]1[C:4]([N:9]2[CH2:10][CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH2:13][CH2:14]2)=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 21904789HCID 21904789, compound

Product 1

HCID 21904722HCID 21904722, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3′-(trifluoromethyl)-3,6-dihydro-2H-1,2′-bipyridine-4-carboxylate (15 mL) in THF (30 mL) was treated with 1N NaOH (27 mL) and stirred for 2 hours. The mixture was treated with additional 1N NaOH (16 mL), stirred for 1 hour, treated with 1N NaOH (14.5 mL), and stirred for 1 hour. The mixture was diluted with water and extracted with CH2Cl2. The aqueous layer was then acidified with concentrated HCl and extracted with CHCl3. The organic layer was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound.

Workup

  1. stirringstirred for 1 hour
  2. stirringstirred for 1 hour
  3. extractionextracted with CH2Cl2
  4. extractionextracted with CHCl3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7add02e6a8d9453c9d075af28d4f71ea
Source dataset
uspto-grants-2008_03
Patent number
US07348343B2

Reaction notes

Loading…