Acetic Acid → 1-[(10-Chloro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-yl)carbonyl]-3-methoxyazetidine

HRID 1885355Notes

Reaction equation

HRID 1885355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#N)[C:3]=1[C:10]1[NH:11][C:12](=[O:30])[C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:14][C:15]=1[C:16]([N:18]1[CH2:21][CH:20]([O:22][CH3:23])[CH2:19]1)=[O:17].C(O)(=O)C>[Zn].O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:10]1=[C:15]([C:16]([N:18]3[CH2:21][CH:20]([O:22][CH3:23])[CH2:19]3)=[O:17])[CH:14]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:12](=[O:30])[N:11]1[CH2:8]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 197854571-[[2-(2-Chloro-6-cyanophenyl)-1,6-dihydro-6-oxo-5-phenyl-3-pyridyl]carbonyl]-3-methoxyazetidine

Product 1

HCID 189570571-[(10-Chloro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-yl)carbonyl]-3-methoxyazetidineYield 29.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

A mixture of 1.17 g of 1-[[2-(2-chloro-6-cyanophenyl)-1,6-dihydro-6-oxo-5-phenyl-3-pyridyl]carbonyl]-3-methoxyazetidine, 0.91 g of zinc powder and 25 ml of acetic acid was heated to boiling under reflux for 15 minutes under argon. The reaction mixture was then poured into 125 ml of water, whereupon the separated crystals were filtered off under suction and washed with water. The aqueous phase was exhaustively extracted with methylene chloride. The combined organic phases were evaporated and the residue was purified with the crystals obtained above. This material was chromatographed on silica gel with methylene chloride/acetone (9:1) and then recrystallized from toluene. There was obtained 0.33 g of 1-[(10-chloro-4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindol-1-yl)carbonyl]-3-methoxyazetidine as yellow crystals with a m.p. of 235°-238°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 minutes under argon
  3. filtrationwere filtered off under suction
  4. washwashed with water
  5. extractionThe aqueous phase was exhaustively extracted with methylene chloride
  6. customThe combined organic phases were evaporated
  7. customthe residue was purified with the crystals
  8. customobtained above
  9. customThis material was chromatographed on silica gel with methylene chloride/acetone (9:1)
  10. customrecrystallized from toluene

Sources & evidence

ORD record
ord-b29f5917d04a4476bacea58498b2c614
Source dataset
uspto-grants-1992_09
Patent number
US05143912

Reaction notes

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