1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 13071762, compound

HRID 2418470Notes

Reaction equation

HRID 2418470 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Cl:18])=[C:12]([F:17])[CH:13]=2)[N:8]([CH2:19][CH2:20]Cl)[CH:7]=1)=[O:5])[CH3:2].C1CCN2C(=NCCC2)CC1>CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Cl:18])=[C:12]([F:17])[CH:13]=2)[N:8]([CH:19]=[CH2:20])[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6212337-Chloro-1-(2-chloroethyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, ethyl ester

Product 1

HCID 13071762HCID 13071762, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a 120 ml of anhydrous dimethyl sulfoxide (DMSO), 6.32 g of 1-(2-chloroethyl)-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester and 2.89 g of 1,8-diazabicyclo[5,4,0]-7-undecene were added and the mixture was heated at 84°-89° C. for 2 hrs. The reaction mixture was concentrated in vacuo and the residue was dissolved in chloroform. The chloroform layer was washed with water and dried. The residue obtained through evaporation of chloroform was recrystallized from ethyl ether to give 3.66 g (65.1% yield) of 1-vinyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester. mp: 146°-149° C.

Workup

  1. temperaturethe mixture was heated at 84°-89° C. for 2 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe chloroform layer was washed with water
  5. customdried
  6. customThe residue obtained through evaporation of chloroform
  7. customwas recrystallized from ethyl ether

Sources & evidence

ORD record
ord-1532107dbffa44fda9a11e8418d196ea
Source dataset
uspto-grants-1984_09
Patent number
US04472579

Reaction notes

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