Aluminium lithium hydride → HCID 68413457, compound

HRID 220270Notes

Reaction equation

HRID 220270 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]([NH:14][CH3:15])=O)[CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][NH:14][CH3:15])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 684150443-furo[2,3-b]pyridin-5-yl-N-methyl-propionamide

Product 1

HCID 68413457HCID 68413457, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.36 g of 3-furo[2,3-b]pyridin-5-yl-N-methyl-propionamide in 10 ml of THF was added dropwise 2.3 ml of a LiAlH4 (2.3M THF) solution at 0° C. The reaction mixture was slowly heated to 60° C. over 1 h and stirred for another 2 h at 60° C. The reaction was quenched by addition of 1M NaOH solution. The resulting mixture was filtrated over a pad of celite, washed with THF and the filtrate was concentrated in vacuo to yield 0.35 g of (3-furo[2,3-b]pyridin-5-yl-propyl)-methyl-amine as brown oil.

Workup

  1. customThe reaction was quenched by addition of 1M NaOH solution
  2. filtrationThe resulting mixture was filtrated over a pad of celite
  3. washwashed with THF
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-869f35c6f2454b4b912f2f442f82da09
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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