HCID 14608782, compound → HCID 14608783, compound

HRID 1650149Notes

Reaction equation

HRID 1650149 reaction equation
[F:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[N:14]3[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]3)=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[O:20])[C:6]=2[CH:21]=1.[H][H]>FC(F)(F)C(O)=O.[Pd]>[F:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[N:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7](=[O:20])[C:6]=2[CH:21]=1

Participants

5

Reactant 2

HCID 14608782HCID 14608782, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14608783HCID 14608783, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 0.5 g of ethyl 8,9-difluoro-6-oxo-6H-benzo[c]quinolizine-5-carboxylate and 0.5 g of 10% palladium-on-carbon in 50 ml of trifluoroacetic acid was shaken under 40 lb. of hydrogen in a Parr apparatus for 2 hours. The mixture was filtered and the solvent evaporated. The concentrate was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was dried followed by adding hexanes to give 0.45 g of the desired product, mp 166°-168° c.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent evaporated
  3. customThe concentrate was partitioned between aqueous sodium bicarbonate and dichloromethane
  4. customThe organic layer was dried
  5. additionby adding hexanes

Sources & evidence

ORD record
ord-6e32d9639fa14631bffe8cb0cb08618d
Source dataset
uspto-grants-1990_05
Patent number
US04923868

Reaction notes

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