Potassium Hydroxide → 4-(Aminomethyl)benzamide

HRID 2114680Notes

Reaction equation

HRID 2114680 reaction equation
[OH-:1].[K+].[NH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1>CC(O)(C)C>[NH2:10][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([C:4]([NH2:3])=[O:1])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 25128184-(Aminomethyl)benzamideYield 66.6%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Powdered potassium hydroxide (340 mg, 6 mmol) was added in one portion to a stirred solution of 4-(aminomethyl)benzonitrile (200 mg, 1.5 mmol) in 2-methyl-2-propanol (20 ml) at reflux under nitrogen. The reaction was heated at reflux for 30 minutes and cooled to room temperature. The mixture was concentrated under reduced pressure and the crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5, by volume) to provide the title compound (150 mg) as a white solid.

Workup

  1. temperatureat reflux under nitrogen
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 30 minutes
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5, by volume)

Sources & evidence

ORD record
ord-68cc664eaaaf48da979c8b5eb8877a7c
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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