Sodium Hydroxide → 4-(Aminomethyl)-2-chloroaniline

HRID 14404

Reaction equation

HRID 14404 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[Cl:16].[OH-].[Na+]>C1COCC1>[NH2:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][NH2:13])=[CH:10][C:9]=1[Cl:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5198964-Amino-3-chlorobenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 218806504-(Aminomethyl)-2-chloroanilineYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium aluminum hydride (2.11 g, 55.6 mmol) in dry THF (50 mL) was added dropwise 4-amino-3-chlorobenzonitrile (3.29 g, 21.6 mmol) in THF (40 mL). The mixture was stirred at RT for 16 hours. Then, 6.0 mL of 1.0 N NaOH solution was added dropwise and the reaction mixture was stirred for 20 min. The solid was filtered off and washed with THF for three times. The solvent was removed by rotavap to give 4-amino-3-chlorobenzylamine as an oily liquid (3.04 g, 90%). 1H NMR (500 MHz, CD3OD): δ 7.18 (d, J=2Hz, 1H), 7.00 (dd, J=8Hz, 2Hz, 1H), 6.78 (d, J=8Hz, 1H), 3.61 (s, 2H).

Workup

  1. stirringthe reaction mixture was stirred for 20 min
  2. filtrationThe solid was filtered off
  3. washwashed with THF for three times
  4. customThe solvent was removed by rotavap

Sources & evidence

ORD record
ord-165a5394ee0844deb8f9d0413dd1b106
Source dataset
uspto-grants-2010_06
Patent number
US07732434B2

Linked notes

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