Undec-4-ene → 1-Cyclopropyl-7-[3-(ethylamino)pyrrolidin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid

HRID 978528Notes

Reaction equation

HRID 978528 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:21][CH2:22]CCCCC=CCCC.C([N:34]1[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35]1)C>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:34]4[CH2:38][CH2:37][CH:36]([NH:39][CH2:21][CH3:22])[CH2:35]4)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 136496Undec-4-eneHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 128619421-Ethylpyrrolidin-3-amine

Product 1

HCID 4703641-Cyclopropyl-7-[3-(ethylamino)pyrrolidin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.80 g (2.8 mmol) of the 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 10 ml of acetonitrile and 0.43 g (2.8 mmol) of 1,8-diazobicyclo [5.4.0], undec-7-ene was added 0.35 g (3.1 mmol) of the N-ethyl-3-aminopyrrolidine. The mixture was refluxed for one hour and stirred overnight. The solids were filtered and washed with ether: acetonitrile (6:1), to give 0.81 g of the title compound, mp 236°-238° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. filtrationThe solids were filtered
  3. washwashed with ether: acetonitrile (6:1)

Sources & evidence

ORD record
ord-59d070f516be47ad90e897cf6931ceed
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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