Sodium Hydroxide → HCID 86684869, compound

HRID 238367Notes

Reaction equation

HRID 238367 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1)[C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.[OH-].[Na+]>O1CCCC1>[CH3:7][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][CH:11]=1)[C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86684868HCID 86684868, compound

Product 1

HCID 86684869HCID 86684869, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Under cooling in an ice bath, lithium aluminum hydride (56 mg) was added to a tetrahydrofuran (3.2 mL) solution of N-methyl-N-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)benzamide (138 mg), and the obtained solution was then heated to reflux at 75° C. for 2.5 hours. Thereafter, a 1 M sodium hydroxide aqueous solution was added to the reaction solution under cooling in an ice bath, and the obtained solution was then stirred at a room temperature for 1.5 hours. Thereafter, the reaction suspension was filtrated with Celite, and the filtrate was then concentrated under a reduced pressure. The residue was diluted with ethyl acetate. The resultant was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=70:30 to 50:50), so as to obtain the title compound (42 mg) in the form of a colorless oily substance.

Workup

  1. temperatureUnder cooling in an ice bath
  2. temperaturethe obtained solution was then heated
  3. temperatureunder cooling in an ice bath
  4. filtrationThereafter, the reaction suspension was filtrated with Celite
  5. concentrationthe filtrate was then concentrated under a reduced pressure
  6. additionThe residue was diluted with ethyl acetate
  7. washThe resultant was washed with a saturated saline
  8. dry with materialwas then dried over anhydrous magnesium sulfate
  9. concentrationfollowed by vacuum concentration
  10. customThe residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=70:30 to 50:50)

Sources & evidence

ORD record
ord-b44251d05c7c4f969554ef8b8e004c8f
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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