Water → [2-Isopropoxy-6-methyl-3-pyridyl]methanamine

HRID 1505228Notes

Reaction equation

HRID 1505228 reaction equation
[CH:1]([O:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]([CH3:13])[N:6]=1)([CH3:3])[CH3:2].C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC>[CH:1]([O:4][C:5]1[C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=[C:7]([CH3:13])[N:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydride2×HCID 216043632-Isopropoxy-6-methyl-nicotinonitrile

Product 1

HCID 61655597[2-Isopropoxy-6-methyl-3-pyridyl]methanamineYield 89.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

The nitrile 32a (1.25 g, 7.12 mmol) solubilized in Et2O (20 mL) and THF (10 mL) was added in small portion to a mixture of LiAlH4 (0.54 g, 2 mol eq) in Et2O (50 mL) stirred at 0° C. Then the mixture was stirred at room temperature overnight. The excess of LiAlH4 was decomposed by water addition at 0° C., the solid formed was filtered, washed with Et2O and the filtrate was separated. The organic phase was anhydrified over Na2SO4 and evaporated to dryness to obtain 33a as yellow oil (1.14 g, 6.35 mmol, 89% Yield) used without further purification.

Workup

  1. stirringThen the mixture was stirred at room temperature overnight
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with Et2O
  5. customthe filtrate was separated
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-85f9c001e53b41529197687bc5573a48
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

Loading…