Aluminium lithium hydride → HCID 67285271, compound

HRID 2111681Notes

Reaction equation

HRID 2111681 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67283788HCID 67283788, compound

Product 1

HCID 67285271HCID 67285271, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(2-Cyanopyridin-4-yl)pyridine (Method 99; 563 mg, 3.11 mmol) was dissolved in anhydrous THF (10 ml) under a nitrogen atmosphere and was cooled to 0° C. LiAlH4 (2.3 ml of a 1M solution in THF, 2.3 mmol) was added dropwise and the reaction was stirred at 0° C. for 3 hours. The reaction was quenched with water (0.1 ml) followed by 15% sodium hydroxide solution (0.1 ml) then water (0.3 ml). The mixture was filtered and the filter pad was washed with methanol. The volatiles were removed from the filtrate by evaporation to give the title compound (570 mg, 99%) as a gum. m/z 186 (MH)+

Workup

  1. customThe reaction was quenched with water (0.1 ml)
  2. filtrationThe mixture was filtered
  3. washthe filter pad was washed with methanol
  4. customThe volatiles were removed from the filtrate by evaporation

Sources & evidence

ORD record
ord-7ac5b323297b41f58e29cef6afcfb5c6
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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