Pyrrolidine → HCID 1208044, compound

HRID 434570Notes

Reaction equation

HRID 434570 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 1208044HCID 1208044, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid (0.43 g), pyrrolidine (1.2 g), and pyridine (3 ml) was refluxed for 6 hours. The solvent was evaporated off. The residue was treated with water, acidified with acetic acid, and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The solid was recrystallized from a mixture of DMF and ethanol and gave 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-pyrrolidinyl)quinoline-3-carboxylic acid (0.34 g), mp 284°-286° C. (decomp.).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe solvent was evaporated off
  3. additionThe residue was treated with water
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated
  8. customThe solid was recrystallized from a mixture of DMF and ethanol

Sources & evidence

ORD record
ord-e18a2dbd9bda4d8d933da8c619b2bb52
Source dataset
uspto-grants-1983_08
Patent number
US04398029

Reaction notes

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