Aluminium lithium hydride → (4-Isopropylpyridin-2-yl)methanamine

HRID 2070925Notes

Reaction equation

HRID 2070925 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]#[N:11])[CH:5]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][NH2:11])[CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 450794854-Isopropylpicolinonitrile

Product 1

HCID 59135389(4-Isopropylpyridin-2-yl)methanamineYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 149 mg (1.01 mmol) of 4-isopropylpicolinonitrile in 7 mL of THF at 0° C. was added 150 mg (3.95 mmol) of LiAlH4. After about 15 min., 250 mg of LiAlH4 was added, and after about 15 min. the ice bath was removed and stirring was continued with warming to r.t. After 40 min., 400 μL of H2O, 400 μL of 15% NaOH (aq), and 1.2 mL of brine were added in succession. The mixture was stirred for 85 min., filtered through Celite, and conc. to give 143 mg of (4-isopropylpyridin-2-yl)methanamine which was used without further purification.

Workup

  1. customafter about 15 min. the ice bath was removed
  2. waitAfter 40 min.
  3. addition400 μL of H2O, 400 μL of 15% NaOH (aq), and 1.2 mL of brine were added in succession
  4. stirringThe mixture was stirred for 85 min.
  5. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-c080f00cdb3448cca8d7c3720b23e52e
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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