Benzoyl Peroxide → 2-[4-(Chloromethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dione

HRID 426236Notes

Reaction equation

HRID 426236 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH:3]=1.[Cl:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:19][CH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 109990494-Methyl-2-phthalimidopyridine

Product 1

HCID 591846992-[4-(Chloromethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dioneYield 28%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-(4-methyl-pyridin-2-yl)-isoindole-1,3-dione (952 mg, 4 mmol)), N-chloro succinimide (640 mg, 4.8 mmol), and benzoyl peroxide (484 g, 2 mmol) in carbon tetrachloride (20 ml) was refluxed for 2 hr. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, dichloromethane:EA (95:5)) to afford 300 mg (28%) of 2-(4-chloromethyl-pyridin-2-yl)-isoindole-1,3-dione as a pale brown solid. m.p. 152-153° C. 1H NMR (200 MHz, CDCl3) δ 4.64 (2H, s), 7.42 (1H, d, J=5.0 Hz), 7.49 (1H, s), 7.80-7.99 (4H, m), 8.68 (1H, d, J=5.0 Hz).

Workup

  1. temperaturewas refluxed for 2 hr
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluent, dichloromethane:EA (95:5))

Sources & evidence

ORD record
ord-550011d735bd4a118a6f8b2eb7a68d8a
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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