Dichloromethane → Benzonitrile, 3-(aminomethyl)-

HRID 1432540Notes

Reaction equation

HRID 1432540 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][N:7]1C(=O)C2=CC=CC=C2C1=O)#[N:2].O.NN.C(Cl)Cl.[OH-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][NH2:7])#[N:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 123753363-((1,3-Dioxoisoindolin-2-yl)methyl)benzonitrile

Product 1

HCID 457594Benzonitrile, 3-(aminomethyl)-Yield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the N-(3-cyanobenzyl)phthalimide (2.70 g, 10.4 mmol) and hydrazine hydrate (2.5 mL, 51 mmol) in MeOH (50 mL) was heated to reflux for 1 h. After cooling at room temperature, CH2Cl2 and aq. 1N NaOH were added. The CH2Cl2 layer was separated, washed with brine, dried over Na2SO4, concentrated in vacuo to give an oil (1.10 g), which was pure enough for the next reaction. MS 133 (M+H) and 116 (M−NH2)

Workup

  1. temperatureto reflux for 1 h
  2. customThe CH2Cl2 layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4aa18941ded04ade93a4d695cb76d9c9
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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