Phthalimide → 2-[(6-Chloropyridin-3-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1494570Notes

Reaction equation

HRID 1494570 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][N:3]=1.ClC1C=CC(CCl)=CN=1.[C:19]1(=[O:29])N[C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[OH-].[K+]>C(O)C.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:22](=[O:24])[C:21]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]3[C:19]2=[O:29])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 14797Potassium HydroxideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 70209275-(Aminomethyl)-2-chloropyridine

Product 1

HCID 143247132-[(6-Chloropyridin-3-yl)methyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

It is known that 2-chloro-5-aminomethyl-pyridine, an intermediate for the preparation of insecticides, is obtained when, in a first step, 2-chloro-5-chloromethyl-pyridine is reacted with phthalimide in the presence of potassium hydroxide, dimethylformamide and ethanol to give N-(2-chloro-pyridin-5-yl-methyl)-phthalimide and, in a second step, the desired 2-chloro-5-aminomethyl-pyridine is liberated from this using hydrazine hydrate in ethanol (cf. EP-A 302,389, p. 23).

Workup

  1. customan intermediate for the preparation of insecticides
  2. customis obtained when

Sources & evidence

ORD record
ord-d7504c18b794492aa5041fb22aed767f
Source dataset
uspto-grants-1991_06
Patent number
US05026864

Reaction notes

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