Sodium Hydroxide → HCID 21904722, compound

HRID 1246722Notes

Reaction equation

HRID 1246722 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-af14734f8ddf4d0da6a78fc8564b227f
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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