Water → (2-(Aminomethyl)phenyl)methanol

HRID 2230802Notes

Reaction equation

HRID 2230802 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH2:9][C:10]1C=C[CH:16]=[CH:15][C:11]=1C([O-])=O)#[N:8].O.[OH-].[Na+].C([O:24][CH2:25][CH3:26])C>>[OH:24][CH2:25][C:26]1[CH:16]=[CH:15][CH:11]=[CH:10][C:9]=1[CH2:7][NH2:8]

Participants

6

Reactant 5

HCID 962Water2×HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 69851902-(Cyanomethyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11275036(2-(Aminomethyl)phenyl)methanol

Procedure

Lithium aluminium hydride (12.4 ml, 1.0M in diethyl ether) was added cautiously to 2-cyanomethylbenzoate (1.00 g, 6.2 mmol) in anhydrous diethyl ether (40 ml) under nitrogen with stirring over 10 min. whilst ensuring the temperature was not greater than 15-25 C. using an ice bath. After the addition was complete the reaction mixture was allowed to warm to 21 C. and then heated at reflux for 16 h. The reaction mixture was cooled to approximately −10 C. It was treated cautiously dropwise with water (0.5 ml), 20% aqueous sodium hydroxide (0.37 ml) and water (1.74 ml). The resultant green heterogeous mixture was filtered and the residue was with diethyl ether (150 ml), the combined washings and filtrate were dried (MgSO4) and solvent was removed in vacuo affording the title compound as a green oil (0.807 g). Mass Spectrum m/z 138 (MH+ for C8H12NO).

Workup

  1. additionAfter the addition
  2. temperatureto warm to 21 C
  3. temperatureand then heated
  4. temperatureat reflux for 16 h
  5. temperatureThe reaction mixture was cooled to approximately −10 C
  6. filtrationThe resultant green heterogeous mixture was filtered
  7. dry with materialthe combined washings and filtrate were dried (MgSO4) and solvent
  8. customwas removed in vacuo

Sources & evidence

ORD record
ord-490ca47ce448413182b239f7d2e8d01a
Source dataset
uspto-grants-2002_07
Patent number
US06426337B1

Reaction notes

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