Water → HCID 64090651, compound

HRID 451567Notes

Reaction equation

HRID 451567 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[C:9]2[C:10]([NH:15]C(=O)C(C)(C)C)=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>C(O)C>[NH2:15][C:10]1[C:9]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[OH:22])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67342290HCID 67342290, compound

Product 1

HCID 64090651HCID 64090651, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-{3-[(4-fluoro-phenyl)-hydroxy-methyl]-pyridin-2-yl}pivalamide (890 mg, 2.94 mmol) in ethanol (44 mL) was added 2 N aqueous sodium hydroxide solution (7.36 mL, 14.7 mmol). The reaction was heated to 100° C. for 5 hours. Water was added and the reaction was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield the title compound as a as a light yellow solid (548 mg, 85%) without further purification.

Workup

  1. extractionthe reaction was extracted twice with ethyl acetate
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-679d1b2f561b452d88c7d4a22663bc74
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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