Pyrrolidine → 6-methoxy-7-[3-(1-pyrrolidyl)propyloxy]-4(1H)-quinolinone

HRID 68534Notes

Reaction equation

HRID 68534 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:16])[CH:11]=[CH:12][NH:13]2)=[CH:8][C:7]=1[O:17][CH3:18].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C(#N)C>[CH3:18][O:17][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[NH:13][CH:12]=[CH:11][C:10]2=[O:16]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 717440127-(3-Chloropropoxy)-6-methoxyquinolin-4-OL

Product 1

HCID 226466186-methoxy-7-[3-(1-pyrrolidyl)propyloxy]-4(1H)-quinolinoneYield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Intermediate V (62 g, 0.232 mol) and tetrahydropyrrole (82.46 g, 1.16 mol) were added to acetonitrile (620 mL). The mixture was heated under reflux for 8 h. After completion of the reaction, a portion of solvent was evaporated off. The reaction vessel was placed in a cold trap. The reaction was filtered by suction. The filtered cake was washed with ethyl acetate to produce a yellow solid (66.74 g) in a yield of 95.3%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 h
  3. customAfter completion of the reaction
  4. customa portion of solvent was evaporated off
  5. customThe reaction vessel was placed in a cold trap
  6. filtrationThe reaction was filtered by suction
  7. washThe filtered cake was washed with ethyl acetate

Sources & evidence

ORD record
ord-9696f82dd01e474d91ff9c7a32ee5d46
Source dataset
uspto-grants-2014_09
Patent number
US08822465B2

Reaction notes

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