Thionyl Chloride → HCID 13472999, compound

HRID 2308810Notes

Reaction equation

HRID 2308810 reaction equation
[Br:1][C:2]1[C:13]2=[C:14]3[N:9]([CH:10]([CH3:15])[CH2:11][CH2:12]2)[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6](=[O:19])[C:5]3=[CH:4][C:3]=1[F:20].S(Cl)(Cl)=O>CN(C)C=O.C1CCCCC1>[Br:1][C:2]1[C:13]2=[C:14]3[N:9]([CH:10]([CH3:15])[CH2:11][CH2:12]2)[CH:8]=[C:7]([C:16]([O:18][CH2:7][CH2:8][N:9]([CH3:14])[CH3:10])=[O:17])[C:6](=[O:19])[C:5]3=[CH:4][C:3]=1[F:20]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 13472993HCID 13472993, compound

Product 1

HCID 13472999HCID 13472999, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8078CyclohexaneSolvent

Procedure

A mixture of 3.0 g of 8-bromo-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, 25 ml of thionyl chloride and 2 drops of N,N-dimethylformamide was heated on a steam bath for 15 minutes. The excess thionyl chloride was removed by evaporation. The residue of solid 8-bromo-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxyl chloride was suspended in 100 ml of dichloromethane, the mixture was stirred and 10 ml of dimethylaminoethanol was added. After 10 minutes of stirring the solution was washed with sodium bicarbonate solution, then dried over magnesium sulfate. The solution was treated with decolorizing charcoal, filtered and concentrated to provide an oil. When cyclohexane was added, tan solid N,N-dimethylaminoethyl 8-bromo-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate formed. This product was dissolved in 50 ml of hot isopropanol, treated with decolorizing charcoal and filtered. A solution of isopropanol saturated with hydrogen chloride gas was added until the mixture became acidic. The white precipitate that formed was N,N-dimethylaminoethyl 8-bromo-6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate hydrochloride, m.p. 250° C. (dec.)

Workup

  1. temperaturewas heated on a steam bath for 15 minutes
  2. customThe excess thionyl chloride was removed by evaporation
  3. addition10 ml of dimethylaminoethanol was added
  4. stirringAfter 10 minutes of stirring the solution
  5. washwas washed with sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. additionThe solution was treated with decolorizing charcoal
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto provide an oil

Sources & evidence

ORD record
ord-d6730342734046d78a23ace24ba80ecc
Source dataset
uspto-grants-1987_09
Patent number
US04691016

Reaction notes

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