Sodium Hydroxide → HCID 11391512, compound

HRID 856748Notes

Reaction equation

HRID 856748 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:11])=[C:6]([C:18]([F:21])([F:20])[F:19])[CH:5]=1)=[N+]=[N-].[H-].[Li+].[Al+3].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[OH:11])=[C:6]([C:18]([F:21])([F:19])[F:20])[CH:5]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 86595198HCID 86595198, compound

Product 1

HCID 11391512HCID 11391512, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of [4-azido-2-(trifluoromethyl)phenyl](2-pyridyl)methanone (2.0 g) in THF (20 ml) was added dropwise a solution of aluminum lithium hydride (520 mg) in. THF (20 ml) at 0° C. under nitrogen atmosphere. After finishing the dropping, the mixture was allowed to be at room temperature, and the mixture was stirred for 1 hour. Water (0.52 ml), 15% aqueous solution of sodium hydroxide (0.52 ml) and water (1.6 ml) were sequentially added to the mixture at 0° C., and the mixture was allowed to be at room temperature and the mixture was stirred overnight. Magnesium sulfate was added to the mixture, and the unnecessary substances were filtered off. The solvent was distilled off under reduced pressure and the obtained residue was recrystallized from hexane-ethyl acetate, to give [4-amino-2-(trifluoromethyl)phenyl](2-pyridyl)methanol (1.51 g) as colorless crystals.

Workup

  1. customat 0° C.
  2. customto be at room temperature
  3. customto be at room temperature
  4. stirringthe mixture was stirred overnight
  5. filtrationthe unnecessary substances were filtered off
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-ea42d737654542aea3b2bfe0b3b49c1d
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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