1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Ethyl-6,8-difluoro-7-[3-[(2-hydroxyethylamino)methyl]pyrrolidin-1-yl]-4-oxo-quinoline-3-carboxylic acid

HRID 868038Notes

Reaction equation

HRID 868038 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].N12CCCN=C1CCCCC2.[NH:31]1[CH2:35][CH2:34][CH:33]([CH2:36][NH:37][CH2:38][CH2:39][OH:40])[CH2:32]1>C(#N)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:31]3[CH2:35][CH2:34][CH:33]([CH2:36][NH:37][CH2:38][CH2:39][OH:40])[CH2:32]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 134918032-[(3-Pyrrolidinylmethyl)amino]ethanol

Product 1

HCID 4614271-Ethyl-6,8-difluoro-7-[3-[(2-hydroxyethylamino)methyl]pyrrolidin-1-yl]-4-oxo-quinoline-3-carboxylic acidYield 79.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.50 g (1.84 mmole) of 1-ethyl-6,7,8-trifluoro-4-oxo-quinoline-3-carboxylic acid, 5 ml acetonitrile, 0.28 g (1.84 mmole) 1,8-diazabicyclo[5.4.0]undec-7-ene and 0.28 g (1.94 mmole) of 2-[(3-pyrrolidinylmethyl)amino]ethanol was refluxed one hour and then stirred at room temperature overnight. The reaction was filtered and the precipitate washed with ether until dry to give 0.58 g of 1-ethyl-6,8-difluoro-1,4-dihydro-7-[3-[[(2-hydroxyethyl)amino]methyl]-1-pyrrolidinyl]-4-oxo-3-quinoline carboxylic acid, mp 215°-216° C.

Workup

  1. temperaturewas refluxed one hour
  2. filtrationThe reaction was filtered
  3. washthe precipitate washed with ether
  4. customuntil dry

Sources & evidence

ORD record
ord-f0aada88fb98493181efd2c510d6b692
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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