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

HRID 912926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 912926
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7e22f1270dad4d429ecf9ccc44cd3225
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026241B2

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