Water → 2-(5,6-Dichloro-pyridin-3-ylmethyl)-isoindole-1,3-dione

HRID 730867Notes

Reaction equation

HRID 730867 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([Cl:10])[C:6]([Cl:9])=[N:7][CH:8]=1.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K].O>CN(C=O)C>[Cl:10][C:5]1[CH:4]=[C:3]([CH2:2][N:15]2[C:11](=[O:21])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:16])[CH:8]=[N:7][C:6]=1[Cl:9]

Participants

5

Reactant 3

HCID 962WaterHCID 219623285-(Bromomethyl)-2,3-dichloropyridineHCID 24194345Phthalimide potassium salt

Product 1

HCID 859654402-(5,6-Dichloro-pyridin-3-ylmethyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromomethyl-2,3-dichloro-pyridine from step (a) above (121 mg, 0.5 mmol) and potassium phthalimide (139 mg, 0.75 mmol, Aldrich) in DMF (1 mL) was stirred at room temperature for 30 min. Water (5 mL) was added and the mixture was extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (5 mL) and brine (5 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was suspended in 20% EtOAc/hexane, and filtered. The solid was washed with 20% EtOAc/hexane and dried in vacuo to give the title compound. MS (ESI, pos. ion) m/z: 307 (M+1).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts were washed with water (5 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. filtrationfiltered
  7. washThe solid was washed with 20% EtOAc/hexane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-0e627fed29404a6298887d696de8234b
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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