Aluminium lithium hydride → HCID 178426053, compound

HRID 1501066Notes

Reaction equation

HRID 1501066 reaction equation
[OH:1][C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([CH3:14])[C:3]=1[C:4]#[N:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:5][CH2:4][C:3]1[C:2]([OH:1])=[N:9][C:8]([C:10]([F:11])([F:12])[F:13])=[CH:7][C:6]=1[CH3:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178426052HCID 178426052, compound

Product 1

HCID 178426053HCID 178426053, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxy-4-methyl-6-(trifluoromethyl)nicotinonitrile (1 g, 5 mmol) in tetrahydrofuran (100 mL) was added lithium aluminum hydride (0.3 g, 7.9 mmol). The mixture was stirred at room temperature for 24 hours. The mixture was filtered, acidified and concentrated. To the residue, water (50 mL) was added and then extracted with dichloromethane (2*50 mL). The combined organic phase was separated, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (silica gel, methanol/dichloromethane=1:5, 1% NH3) to give 3-(aminomethyl)-4-methyl-6-(trifluoromethyl)pyridin-2-ol as a yellow oil (0.8 g, 78%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. additionTo the residue, water (50 mL) was added
  4. extractionextracted with dichloromethane (2*50 mL)
  5. customThe combined organic phase was separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography (silica gel, methanol/dichloromethane=1:5, 1% NH3)

Sources & evidence

ORD record
ord-27e692d2591843ee92ec8066fc028d01
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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