Methyl 2-cyanobenzoate → (2-(Aminomethyl)phenyl)methanol

HRID 582576Notes

Reaction equation

HRID 582576 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[N:11].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[NH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 582554Methyl 2-cyanobenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11275036(2-(Aminomethyl)phenyl)methanolYield 81.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of methyl-2-cyanobenzoate (10 g, 62.11 mmol) in ethyl ether (300 mL) was added dropwise to a slurry of lithium aluminum hydride in ethyl ether (200 mL). After the addition was complete, more ether was added (200 mL) and the mixture heated at reflux for 2 h. The cooled reaction mixture was quenched by careful addition of succesive amounts of water (7.1 mL), 1N sodium hydroxide solution (7.1 mL) and water (21.3 mL). The reaction was filtered and evaporated to give 6.96 g (50.8 mmol) of 2-(aminomethyl)benzyl alcohol. This material was carried on without further purification.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture heated
  3. temperatureat reflux for 2 h
  4. customThe cooled reaction mixture
  5. customwas quenched by careful addition of succesive amounts of water (7.1 mL), 1N sodium hydroxide solution (7.1 mL) and water (21.3 mL)
  6. filtrationThe reaction was filtered
  7. customevaporated

Sources & evidence

ORD record
ord-9961a782de6f450db167dc0f29472df2
Source dataset
uspto-grants-1999_07
Patent number
US05925635

Reaction notes

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