Phthalimide → HCID 22022171, compound

HRID 1181283Notes

Reaction equation

HRID 1181283 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).

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-38643aaf850343648271f619d7ee9d55
Source dataset
uspto-grants-2007_10
Patent number
US07285561B2

Reaction notes

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