1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-[3-(Aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid

HRID 622506Notes

Reaction equation

HRID 622506 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.[NH:21]1[CH2:25][CH2:24][CH:23]([CH2:26][NH2:27])[CH2:22]1>C(#N)C>[NH2:27][CH2:26][CH:23]1[CH2:24][CH2:25][N:21]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:16])[CH2:22]1

Participants

4

Reactant 2

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 50687753-Pyrrolidinemethanamine

Product 1

HCID 4695537-[3-(Aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-quinoline-3-carboxylic acidYield 94.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.00 g (3.53 mmole) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 10 ml of acetonitrile, 0.54 g (3.5 mmole) 1,8-diazobicyclo[5.4.0]undec-7-ene, and 0.37 g (3.7 mmole) of 3-pyrrolidinemethanamine is refluxed one hour, then stirred at room temperature overnight. The reaction mixture is then filtered and the precipitate washed with ethyl ether until dry to yield 1.21 g (94.5%) of the title compound, mp 232°-235° C.

Workup

  1. temperatureis refluxed one hour
  2. filtrationThe reaction mixture is then filtered
  3. washthe precipitate washed with ethyl ether
  4. customuntil dry

Sources & evidence

ORD record
ord-311a4310739445c0b6ca9b148777928a
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Reaction notes

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