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

HRID 256683

반응식

HRID 256683 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 2724286Titanium(IV)ethoxide촉매HCID 244Benzyl Alcohol용매HCID 962Water용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-21cb10d88c6e42f7b4b0e618b702c92c
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258387

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