Aluminium lithium hydride → 5-(Aminomethyl)-2-(trifluoromethyl)pyridine

HRID 2071000Notes

Reaction equation

HRID 2071000 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:10]=1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:13][C:11]([F:12])([F:14])[C:8]1[N:9]=[CH:10][C:5]([CH2:4][NH2:1])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866017575-(Azidomethyl)-2-(trifluoromethyl)pyridine

Product 1

HCID 27377185-(Aminomethyl)-2-(trifluoromethyl)pyridineYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(azidomethyl)-2-(trifluoromethyl)pyridine (2.6 g, 12.86 mmol) in THF at −78° C. was added LAH (0.54 g, 14.2 mmol). The resulting mixture was stirred for 15 min. and warmed to room temperature for one hour. Then the reaction was quenched with saturated aqueous NH4Cl and stirred for a couple of hours. Anhydrous Na2SO4 was added to make the mixture clear two phases, filtered and washed with EtOAc. The combined organic solution was concentrated to provide (6-(trifluoromethyl)pyridin-3-yl)methanamine as a red syrup (2.1 g). 1H NMR (300 MHz, CDCl3+CD3OD), d: 8.729 (s, 1H), 7.928 (d, J=9.1 Hz, 1H), 7.706 (d, J=9.1 Hz, 1H), 4.054 (s, 2H).

Workup

  1. customThen the reaction was quenched with saturated aqueous NH4Cl
  2. stirringstirred for a couple of hours
  3. additionAnhydrous Na2SO4 was added
  4. filtrationfiltered
  5. washwashed with EtOAc
  6. concentrationThe combined organic solution was concentrated

Sources & evidence

ORD record
ord-d0c3bc7110394d1fbdef21b4247913b9
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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