2-Chloro-5-(chloromethyl)pyridine → 2-[(6-Chloropyridin-3-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 483348Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.[K]>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:14]2[C:13](=[O:15])[C:12]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]3[C:10]2=[O:20])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

2-Chloro-5-chloromethylpyridine (8.1 g, 0.05 mol) and potassium phthalimide (10.2 g, 0.055 mol) were mixed together at ambient temperature (20° C.) and the resulting mixture was then heated with stirring at 160° C. for 12 hours. The reaction mixture was then cooled to ambient temperature (20° C.) and dichloromethane was added until most of the solid residue had dissolved. The dichloromethane extract was then washed with water (2×150 ml) and brine (1×200 ml), dried using magnesium sulphate, and evaporated under reduced pressure to give a light-brown solid. The title product, N-(6-chloro-3-pyridylmethyl) phthalimide, was isolated from this solid by flash chromatography using silica gel, 230 to 400 US mesh (0.062 mm to 0.037 mm), with 10% v/v ether/ dichloromethane as eluent, as a buff solid (10.70 g, 78.5%), mp 140° to 142° C.

Workup

temperaturethe resulting mixture was then heated
additionwas added until most of the solid residue
dissolutionhad dissolved
extractionThe dichloromethane extract
washwas then washed with water (2×150 ml) and brine (1×200 ml)
customdried
customevaporated under reduced pressure
customto give a light-brown solid

Sources & evidence

ORD record: ord-7302564473bf4a568aabbd8983a67672
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05225423

Reaction notes

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