Pyrrolidine → HCID 14839350, compound

HRID 2165667Notes

Reaction equation

HRID 2165667 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:16])[C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>CN1CCCC1.CCOCC>[CH2:1]([N:3]1[C:12]2[C:7](=[C:8]([F:16])[C:9]([F:15])=[C:10]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[C:11]=2[F:13])[C:6](=[O:17])[C:5]([C:18]([OH:20])=[O:19])=[CH:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 138510191-Ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 14839350HCID 14839350, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 84541-MethylpyrrolidineSolvent

Procedure

A 200 mg portion of 1-ethyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid was dissolved in 1 ml of 1-methylpyrrolidine with warming. A 130 mg portion of pyrrolidine was added dropwise, the reaction was allowed to stand one hour and then diluted with ether. The solid was collected, washed with ether and hexane, dried and recrystallized from a mixture of dichloromethane-acetone, giving 140 mg of the desired product as white crystals, mp >320° C.

Workup

  1. temperaturewith warming
  2. customThe solid was collected
  3. washwashed with ether and hexane
  4. customdried
  5. customrecrystallized from a mixture of dichloromethane-acetone

Sources & evidence

ORD record
ord-523ca8acb9274e1aa4e35dd31255190f
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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