Water → 2-(aminomethyl)-4-chloroaniline

HRID 2118012Notes

Reaction equation

HRID 2118012 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:5][CH2:4][C:3]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 800192-Amino-5-chlorobenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 15152782-(aminomethyl)-4-chloroanilineYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Amino-5-chloro-benzonitrile (9.0 g, 59 mmol) in tetrahydrofuran (100 ml) was added dropwise to an ice cooled 1 molar solution of lithium aluminium hydride (100 ml) in tetrahydrofuran and the reaction mixture was stirred at room temperature for 18 hours. Water (10 ml) was added dropwise. The resulting emulsion was dried over magnesium sulphate, filtered and evaporated under reduced pressure to give the title compound as a white solid (4.56 g).

Workup

  1. dry with materialThe resulting emulsion was dried over magnesium sulphate
  2. filtrationfiltered
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-218aa652dcd14ad5924f8196d2ea12a1
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

Loading…