Ethyl-pyrrolidin-3-ylmethyl-amine → 6,8-Difluoro-4-hydroxy-3-quinolinecarboxylic acid

HRID 978543Notes

Reaction equation

HRID 978543 reaction equation
C1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([F:19])=[C:14](F)[C:15]=3[F:17])[C:10](=[O:20])[C:9]([C:21]([OH:23])=[O:22])=[CH:8]2)CCCCC1.C(NCC1CCNC1)C>C(#N)C>[F:19][C:13]1[CH:12]=[C:11]2[C:16](=[C:15]([F:17])[CH:14]=1)[NH:7][CH:8]=[C:9]([C:21]([OH:23])=[O:22])[C:10]2=[O:20]

Participants

4

Reactant 2

HCID 13491786Ethyl-pyrrolidin-3-ylmethyl-amineHCID 137728341-Cyclohexyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 51078606,8-Difluoro-4-hydroxy-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.80 g (2.46 mmol) of 1-cyclohexyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 15 ml of acetonitrile was added 0.37 g (2.46 mmol) of 1,8-diazobicyclo[5.4.0]undec7-ene and 0.33 g (2.58 mmol) of 3-[(ethylamino)methyl]pyrrolidine. The mixture was refluxed for one hour, cooled, filtered, and the solids washed with ether to give 0.86 g of 1-cyclohexyl-7-[3-(ethylamino)methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 194°-196° C.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe solids washed with ether

Sources & evidence

ORD record
ord-efe03fb50eb74ee09c1c97e66e602a40
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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