Aluminium lithium hydride → 3-(Aminomethyl)-2,6-dichloro-5-fluoroaniline

HRID 450331Notes

Reaction equation

HRID 450331 reaction equation
[Cl:1][C:2]1[C:10]([NH2:11])=[C:9]([Cl:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([NH2:6])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:11][C:10]1[C:2]([Cl:1])=[C:3]([CH:7]=[C:8]([F:13])[C:9]=1[Cl:12])[CH2:4][NH2:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866744963-Amino-2,4-dichloro-5-fluorobenzamide

Product 1

HCID 825077343-(Aminomethyl)-2,6-dichloro-5-fluoroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,4-Dichloro-5-fluoro-3 amino-benzamide (6.00 g, 26.9 mmol) in THF (175 mL) is added dropwise to LiAlH4 (1 M in THF, 28.0 mL) in THF (175 mL). The reaction mixture is stirred for 1 h at rt and 5 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, the filtrate is concentrated, diluted with Et2O and the precipitate is collected.

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
  6. additiondiluted with Et2O
  7. customthe precipitate is collected

Sources & evidence

ORD record
ord-eb0c9a939d774358996ac3fe406ed8e9
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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