Water → 2-(Aminomethyl)-6-methylaniline

HRID 1393948Notes

Reaction equation

HRID 1393948 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[NH2:6][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 142218072-Amino-3-methylbenzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 534408702-(Aminomethyl)-6-methylanilineYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of argon, a solution 2-amino-3-methylbenzamide (1.2 g, 80 mmol) in THF (25 ml) was added to a suspension of LiAlH4 (1.52 g, 40 mmol) in THF (25 ml) over 20 min. The suspension was heated to reflux (4 h). For workup, the mixture was cooled to 0° C., and 1.5 ml H2O, 3 ml 4n NaOH, and 3 ml H2O were added subsequently. The suspension was dried (Na2SO4), and evaporated under reduced pressure. The title compound (338 mg, 31%) was isolated from the residue by chromatographic purification (silica gel, CH2Cl2/MeOH (2M NH3)=9:1).

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux (4 h)
  3. dry with materialThe suspension was dried (Na2SO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9deced90cd8a4b07a7e292ea4c3c9c40
Source dataset
uspto-grants-2008_03
Patent number
US07348332B2

Reaction notes

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