Aluminium lithium hydride → 3-(Aminomethyl)-2,6-dichloroaniline

HRID 1189608Notes

Reaction equation

HRID 1189608 reaction equation
[NH2:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH2:7])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:2]1[C:3]([Cl:12])=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:5][NH2:7]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 586254673-Amino-2,4-dichlorobenzamide

Product 1

HCID 568399683-(Aminomethyl)-2,6-dichloroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Amino-2,4-dichloro-benzamide (2.00 g, 9.8 mmol) in THF (45 mL) is added dropwise to LiAlH4 (1 M in THF, 24.4 mL) in THF (45 mL). The reaction mixture is stirred for 1 h at rt and 10 h at reflux. Excess LiAlH4 is destroyed under cooling as described by L. F. Fieser & M. Fieser Vol 1, p 584 Wiley 1967. After 30 min the mixture is filtered and the filtrate is concentrated to give the sub-title compound.

Workup

  1. temperatureat reflux
  2. customExcess LiAlH4 is destroyed
  3. temperatureunder cooling
  4. filtrationAfter 30 min the mixture is filtered
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-87f1575f6e6b4dd0b3a2969b876de590
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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