Lithium Hydroxide → HCID 11665862, compound

HRID 1591576Notes

Reaction equation

HRID 1591576 reaction equation
[OH-].[Li+].[NH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[CH3:11])[N:7]=[C:6]([C:14]([O:16]C)=[O:15])[C:5]=1[Cl:18]>O.O1CCCC1>[NH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[CH3:11])[N:7]=[C:6]([C:14]([OH:16])=[O:15])[C:5]=1[Cl:18]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58996249HCID 58996249, compound

Product 1

HCID 11665862HCID 11665862, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide (159 mg, 1.27 mmol) in water (6 mL) was added to a solution of methyl 4-amino-3-chloro-6-(1,1-difluroethyl)-pyridine-2-carboxylate (159 mg, 0.63 mmol) in tetrahydrofuran (6 mL). The mixture was vigorously stirred at room temperature overnight and was then concentrated to near dryness. After adding water, the reaction mixture was washed once with ethyl acetate to remove unreacted starting material. The aqueous layer was then acidified to pH<3 with 1N HCl and extracted with ethyl acetate. The organic layer was dried (MgSO4), concentrated and the residue triturated with cold hexane to provide 4-amino-3-chloro-6-(1,1-difluoroethyl)-pyridine-2-carboxylic acid (105 mg, 0.44 mmol) as a white solid; 1H NMR (DMSO-d6): δ 7.02 (s, 1H), 6.94 (br.s, 2H), 1.90 (t, 3H).

Workup

  1. concentrationwas then concentrated
  2. additionAfter adding water
  3. washthe reaction mixture was washed once with ethyl acetate
  4. customto remove unreacted
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated
  8. customthe residue triturated with cold hexane

Sources & evidence

ORD record
ord-8785fa3944e243839f9cc3ef1f502889
Source dataset
uspto-grants-2007_11
Patent number
US07291580B2

Reaction notes

Loading…