1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 3-Quinolinecarboxylic acid, 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-((methylamino)methyl)-1-pyrrolidinyl)-4-oxo-

HRID 868072Notes

Reaction equation

HRID 868072 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][NH:22][CH2:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1>C(#N)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([N:26]4[CH2:27][CH2:28][CH:24]([CH2:23][NH:22][CH3:21])[CH2:25]4)[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

Participants

4

Reactant 2

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 13491795N-Methyl-1-(pyrrolidin-3-yl)methanamine

Product 1

HCID 4834173-Quinolinecarboxylic acid, 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-((methylamino)methyl)-1-pyrrolidinyl)-4-oxo-Yield 76.7%

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 N-methyl-3-pyrrolidinemethanamine. The mixture was refluxed for one hour and stirred overnight. The solids were filtered and washed with acetonitrile:ether (1:6) to give 0.81 g of the title compound, mp 265°-267° C.

Workup

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

Sources & evidence

ORD record
ord-ae5fabfd04c34723896ae6a83a30ff5e
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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