Pyrrolidine → HCID 22624029, compound

HRID 566995Notes

Reaction equation

HRID 566995 reaction equation
[C:1]([NH:4][C:5]1[C:10]2[C:11](=[O:24])[N:12]([O:20][CH2:21][CH:22]=[CH2:23])[C:13](=[O:19])[C:14]3=[CH:15][CH:16]=[C:17]([Cl:18])[C:8]([C:9]=23)=[C:7](Cl)[CH:6]=1)(=[O:3])[CH3:2].[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>C(#N)C>[C:1]([NH:4][C:5]1[C:10]2[C:11](=[O:24])[N:12]([O:20][CH2:21][CH:22]=[CH2:23])[C:13](=[O:19])[C:14]3=[CH:15][CH:16]=[C:17]([Cl:18])[C:8]([C:9]=23)=[C:7]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 22624044HCID 22624044, compound

Product 1

HCID 22624029HCID 22624029, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A near solution of 4-acetylamino-2-allyloxy-6,7-dichlorobenzo[de]isoquinoline-1,3-dione (0.3 g, 0.8 mmol, from Example G4), pyrrolidine (0.16 g, 2.2 mmol), and 15 mL of acetonitrile was heated from room temperature to reflux over 0.5 hour. The solvent was removed in vacuo and the residue partitioned between dichloromethane and water. The organic layer was washed with water, dried, and evaporated in vacuo to give 0.26 g of the title compound.

Workup

  1. customwas heated from room temperature
  2. temperatureto reflux over 0.5 hour
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between dichloromethane and water
  5. washThe organic layer was washed with water
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c7586c1e60b4be49ba9a7b41bf90a01
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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