Hydrochloric Acid → Benzyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate

HRID 256683

反応式

HRID 256683 の反応式
[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3.Cl>C(O)C1C=CC=CC=1.O.CCO.CCO.CCO.CCO.[Ti]>[O:1]=[C:2]1[N:7]2[CH2:8][C:9]3[C:14]([C:6]2=[C:5]([C:15]([O:17][CH2:18][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:16])[CH:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 15640822Methyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate

生成物 1

HCID 18957067Benzyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate収率 143.5%

試薬・触媒・溶媒 3

HCID 2724286Titanium(IV)ethoxide触媒HCID 244Benzyl Alcohol溶媒HCID 962Water溶媒

実験手順

A solution of 1.62 9 of tetraethyl orthotitanate in 71 ml of benzyl alcohol was treated with 4.52 g of methyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate and stirred at 115°-120° under argon for 3 hours. The reaction mixture was then cooled, stirred with 71 ml of 1N hydrochloric acid for 1 hour, diluted with 350 ml of water and extracted several times with methylene chloride. The organic phases were washed with saturated sodium hydrogen carbonate solution, dried over sodium sulphate, filtered and evaporated. The residue was stirred in 710ml of diethyl ether for 1 hour, suction filtered and the material obtained was dried in a vacuum. There was obtained 4.02g of benzyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate as yellowish crystals with a m.p. of 229°.

後処理

  1. temperatureThe reaction mixture was then cooled
  2. extractionextracted several times with methylene chloride
  3. washThe organic phases were washed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. stirringThe residue was stirred in 710ml of diethyl ether for 1 hour
  8. filtrationsuction filtered
  9. customthe material obtained
  10. customwas dried in a vacuum

出典と根拠

ORDレコード
ord-21cb10d88c6e42f7b4b0e618b702c92c
出典データセット
uspto-grants-1993_11
特許番号
US05258387

関連ノート

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