HCID 13203249, compound → HCID 13191947, compound

HRID 1995323Notes

Reaction equation

HRID 1995323 reaction equation
[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[N:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1>FC(F)(F)C(O)=O.[Pd]>[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([OH:18])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[C:3]=1[N:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 13203249HCID 13203249, compound

Product 1

HCID 13191947HCID 13191947, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3.6 g of 6,7-dihydro-9-fluoro-5-methyl-1-oxo-8-(1-pyrryl)-1H,5H-benzo[ij]quinolizine-2-carboxylic acid in 50 ml of trifluoroacetic acid was added 2.0 g ten percent palladium on charcoal. The mixture was hydrogenated on a Paar apparatus for two hours at 50 psi at 50° C. The mixture was filtered, and the filtrate was evaporated. The residue was mixed with 50 ml of water and the pH adjusted to 5 by the addition of ten percent sodium hydroxide solution and acetic acid. The precipitate obtained was recrystallized from aqueous N,N-dimethylformamide (80%) to provide tan crystals of 6,7-dihydro-9-fluoro-5-methyl-1-oxo-8-(1-pyrrolidyl)-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, m.p. 243°-245° C. Analysis: Calculated for C18H19FN2O3 : %C, 65.5; %H, 5.8; %N, 8.5; Found: %C, 65.8; %H, 5.8; %N, 8.5. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. additionThe residue was mixed with 50 ml of water
  4. additionthe pH adjusted to 5 by the addition of ten percent sodium hydroxide solution and acetic acid
  5. customThe precipitate obtained
  6. customwas recrystallized from aqueous N,N-dimethylformamide (80%)

Sources & evidence

ORD record
ord-b914a4765c4348709ccf087b84a7957e
Source dataset
uspto-grants-1983_09
Patent number
US04404207

Reaction notes

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