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

HRID 2379588ノート

反応式

HRID 2379588 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 962Water溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-4132ed1174f84d08a5e40034eadd55de
出典データセット
uspto-grants-1994_11
特許番号
US05362738

反応ノート

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