Aluminium lithium hydride → HCID 42625601, compound

HRID 2236480Notes

Reaction equation

HRID 2236480 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:8]#[N:9].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH2:8][NH2:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 42625599HCID 42625599, compound

Product 1

HCID 42625601HCID 42625601, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3-Methoxymethoxy-4-pyridin-2-yl-benzonitrile (160 mg, 0.67 mmol) is then dissolved in ether (10 mL). The resulting solution is slowly added to a suspension of LiAlH4 (100 mg, 2.6 mmol) in Et2O. After addition, the mixture is stirred for another 10 min before quenched with H2O and 5 N NaOH. After which, EtOAc is added and the organic layer is collected and washed with brine and dried over Na2SO4. Removal of the solvent provided the crude amine, which is used directly in the next step. MS (ESI): 245 (M+1)+1.

Workup

  1. additionAfter addition
  2. custombefore quenched with H2O and 5 N NaOH
  3. additionAfter which, EtOAc is added
  4. customthe organic layer is collected
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-09d8db973e3943dbad1d4a52c511b33e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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