Aluminium lithium hydride → 2-[2-(Aminomethyl)-5-chlorophenoxy]ethan-1-ol

HRID 555716Notes

Reaction equation

HRID 555716 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH2:11][CH2:12][OH:13])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][C:4]=1[O:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 630935884-Chloro-2-(2-hydroxy-ethoxy)benzonitrile

Product 1

HCID 630816402-[2-(Aminomethyl)-5-chlorophenoxy]ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4-chloro-2-fluoro-benzonitrile (1.00 g, 6.43 mmol), ethylene glycol (3.59 mL, 64.3 mmol) and K2CO3 (1.33 g, 9.64 mmol) in DMF (30 mL) is stirred at RT for 12 h. The reaction mixture is quenched by H2O. EtOAc is added and the organic layer is washed with brine, dried over MgSO4. Concentration in vacuo affords the corresponding 4-chloro-2-(2-hydroxy-ethoxy)-benzonitrile. A THF (6 mL) solution of 4-chloro-2-(2-hydroxy-ethoxy)benzonitrile (875 mg, 4.43 mmol) is added to a suspension of LAH (504 mg, 13.2 mmol) in THF (45 mL) at 0° C. The reaction is allowed to stir for 2 h at ambient temperature and then quenched by Na2SO4.10H2O, and the product is isolated by filtration with Celite and washed with THF and dried under reduced pressure to give the title compound as colorless solid; ES-MS: M+=202.1; HPLC: AtRet=1.90 min

Workup

  1. customquenched by Na2SO4.10H2O
  2. customthe product is isolated by filtration with Celite
  3. washwashed with THF
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-41bd014ee5ff4dadb472b377966ec793
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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