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

HRID 2379579Notes

Reaction equation

HRID 2379579 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 2724286Titanium(IV)ethoxideCatalystHCID 244Benzyl AlcoholSolventHCID 962WaterSolvent

Procedure

A solution of 1.62 g 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 710 ml of diethyl ether for 1 hour, suction filtered and the material obtained was dried in a vacuum. There was obtained 4.02 g of benzyl 4,6-dihydro-4-oxo-3-phenylpyrido[2,1-a]isoindole-1-carboxylate as yellowish crystals with a m.p. of 229°.

Workup

  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 710 ml of diethyl ether for 1 hour
  8. filtrationsuction filtered
  9. customthe material obtained
  10. customwas dried in a vacuum

Sources & evidence

ORD record
ord-02adbbf6b5b346588d8e860d51c1e389
Source dataset
uspto-grants-1994_11
Patent number
US05362738

Reaction notes

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