Acetic Acid → Phthalimide

HRID 2055137Notes

Reaction equation

HRID 2055137 reaction equation
CNCC[N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].C(=O)C1C=CC=NC=1.[Na].C(O)(=O)C.C([O-])(O)=O.[Na+]>ClCCl>[C:6]1(=[O:15])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13](=[O:14])[NH:5]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 23511414HCID 23511414, compound

Product 1

HCID 6809PhthalimideYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added nicotinaldehyde (1.5 eq), sodium acetoborohydride (4.5 eq) and acetic acid (1.5 eq). After stirring at room temperature for 1 h, NaHCO3 (sat.) was added to the reaction mixture followed by an extraction with dichloromethane. The organic phase was washed with H2O, NaCl (sat.) (50 ml), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH, and 0.1% TEA (2L) to yield 2-[2-methyl-pyridin-3-ylmethyl-amino)-ethyl]-isoindole-1,3-dione (57%). MH+(296)

Workup

  1. extractionfollowed by an extraction with dichloromethane
  2. washThe organic phase was washed with H2O, NaCl (sat.) (50 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-2672155f48ce4efbb79b4218035bc854
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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