Water → [2-(Aminomethyl)-5-chlorophenyl]methanol

HRID 397483Notes

Reaction equation

HRID 397483 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:18]#[N:19])=[C:12]([CH:17]=1)[C:13](OC)=[O:14].O.[OH-].[Na+]>C1COCC1>[NH2:19][CH2:18][C:11]1[CH:10]=[CH:9][C:8]([Cl:7])=[CH:17][C:12]=1[CH2:13][OH:14]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12052442Methyl 5-chloro-2-cyanobenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12052443[2-(Aminomethyl)-5-chlorophenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To LAH (1 M/Et2O, 104.4 ml, 104.4 mmol) in anhydrous THF (300 ml) at 0° C. was added methyl 5-chloro-2-cyanobenzoate (9.28 g, 0.512 mmol) maintaining the temperature below 20° C. After one half hour, quenched at OC with water (3.97 ml), NaOH (1N, 11.9 ml, 11.9 mmol) and water (3.97 ml). A precipitate was filtered out and washed with THF. The filtrate was concentrated in vacuo and was used immediately in the next step.

Workup

  1. temperaturemaintaining the temperature below 20° C
  2. waitAfter one half hour
  3. filtrationA precipitate was filtered out
  4. washwashed with THF
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7fc46edf7e1b46b690ac33f7d5d055ae
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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