1,8-Diazabicyclo(5.4.0)undec-7-ene → 6,8-Difluoro-4-hydroxy-3-quinolinecarboxylic acid

HRID 978495Notes

Reaction equation

HRID 978495 reaction equation
C([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)C.C(NCC1CCNC1)C.N12CCCN=C1CCCCC2>C(#N)C>[F:15][C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([F:13])[CH:10]=1)[NH:3][CH:4]=[C:5]([C:17]([OH:19])=[O:18])[C:6]2=[O:16]

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 13491786Ethyl-pyrrolidin-3-ylmethyl-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 22.50 g (83.03 mmole) 1-ethyl-1,4-dihydro-4-oxo-6,7,8-trifluoro-3-quinolinecarboxylic acid, 225 ml acetonitrile, 11.25 g (87.08 mmole) N-ethyl-3-pyrrolidinemethanamine and 12.6 g (83.03 mmole) 1,8-diazabicyclo[5.4.0]undec-7-ene was refluxed 1 hour then was stirred at room temperature overnight. The solid was filtered and washed with ether to give 26.33 g of 1-ethyl-7-[3-(ethylamino)-methyl]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 208°-210° C.

Workup

  1. temperaturewas refluxed 1 hour
  2. filtrationThe solid was filtered
  3. washwashed with ether

Sources & evidence

ORD record
ord-5a189f56e2544feca1050a2625bbd103
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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