Thionyl Chloride → 1,10a-Dihydro-7-fluoropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dione

HRID 1906450Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:13](=[O:14])[CH2:12][CH2:11][CH:10]2[C:15]([OH:17])=O)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[C:15](=[O:17])[CH:10]3[CH2:11][CH2:12][C:13](=[O:14])[N:9]3[CH2:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 50.00 g of (±)-1-[(3-fluorophenyl)-methyl]-5-oxo-2-pyrrolidine carboxylic acid in sieve dried dichloromethane (450 ml), 27.48 g of thionyl chloride was added, and the resultant solution was stirred and refluxed for 5 hours. An infrared spectrum of the solution indicated the presence of the acid chloride. After standing overnight at ambient temperature, the solution was chilled to 5° C. and 84 g of aluminum chloride was added in portions with vigorous stirring. The reaction was exothermic and there was a slow evolution of gas. The mixture was stirred at ambient temperature for 3 hours. The reaction was quenched by the addition of ice chips and water. The two phases of the mixture were separated and the aqueous phase was extracted with dichloromethane (4×150 ml). The combined organic phase was dried (Na2SO4) and concentrated to a solid (69.73 g).

Workup

temperaturerefluxed for 5 hours
customThe reaction was quenched by the addition of ice chips and water
customThe two phases of the mixture were separated
extractionthe aqueous phase was extracted with dichloromethane (4×150 ml)
dry with materialThe combined organic phase was dried (Na2SO4)
concentrationconcentrated to a solid (69.73 g)

Sources & evidence

ORD record: ord-cddf04cfe0364795b7d1e12d9fa36cb2
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04652567

Reaction notes

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