Pyrrolidine → HCID 22624029, compound

HRID 278984Notes

Reaction equation

HRID 278984 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-3f1f7d11fdc74adfb034900984574112
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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