Phthalimide → HCID 22022171, compound

HRID 497144Notes

Reaction equation

HRID 497144 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=C12.O.[NH2:13]N>CO.ClCCl>[NH2:13][CH2:10][CH2:9][C:8]1[C:1](=[O:11])[NH:5][CH:4]=[CH:3][CH:7]=1

Participants

5

Reactant 2

HCID 6809PhthalimideHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 22022171HCID 22022171, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1.2 g (2.5 mmol) of phthalimide 4 in 100 ml of methanol was added 6 ml of hydrazine monohydrate. This was stirred at room temperature overnight upon which the suspension turned into a clear yellow solution. The mixture was concentrated and residue was diluted with water and extracted with chloroform. The organic solution was washed with brine and dried (MgSO4), and the residue was purified by column chromatography with silica eluting with 10% methanol in dichloromethane affording 0.48 g of the aminoethyl-pyridone 5 (55% yield). Step 3

Workup

  1. concentrationThe mixture was concentrated
  2. additionresidue was diluted with water
  3. extractionextracted with chloroform
  4. washThe organic solution was washed with brine
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-a9b81eb7f4004228ac8baf30901de350
Source dataset
uspto-grants-2005_09
Patent number
US06949560B2

Reaction notes

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