Hydrogen Bromide → HCID 23284711, compound

HRID 369268Notes

Reaction equation

HRID 369268 reaction equation
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([F:30])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[C:16]([O:18]C)[C:15]([F:20])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22])[CH:9]=[C:8]([C:24]([O:26]CC)=[O:25])[C:7]2=[O:29].Br>C(O)(=O)C>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([F:30])[CH:5]=[C:6]2[C:11]=1[N:10]([C:12]1[CH:17]=[C:16]([OH:18])[C:15]([F:20])=[CH:14][C:13]=1[N+:21]([O-:23])=[O:22])[CH:9]=[C:8]([C:24]([OH:26])=[O:25])[C:7]2=[O:29]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 23284751HCID 23284751, compound

Product 1

HCID 23284711HCID 23284711, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 8-chloro-6,7-difluoro-1-(4-fluoro-5-methoxy-2-nitrophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (510 mg) was added to a mixed liquid (1:1, v/v; 5 ml) of 47% hydrobromic acid and acetic acid, aid the mixture was stirred and heated under reflux for 46 hours. The reaction mixture was concentrated under reduced pressure. A process of adding distilled water (5 ml) to the residue and then concentrating the mixture under reduced pressure was conducted twice repeatedly. Distilled water (5 ml) was added to the resultant residue, and deposits were collected by filtration. The deposits were dispersed in ethanol (2 ml) and heated to reflux. The reaction mixture was allowed to cool, and deposits were collected by filtration and washed with ethanol and diisopropyl ether in that order to obtain the title compound (220 mg) as a pale brown powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 46 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionA process of adding
  5. distillationdistilled water (5 ml) to the residue
  6. concentrationconcentrating the mixture under reduced pressure
  7. additionDistilled water (5 ml) was added to the resultant residue, and deposits
  8. filtrationwere collected by filtration
  9. additionThe deposits were dispersed in ethanol (2 ml)
  10. temperatureheated to reflux
  11. temperatureto cool
  12. filtrationdeposits were collected by filtration
  13. washwashed with ethanol and diisopropyl ether in that order

Sources & evidence

ORD record
ord-f363a2f591394bc98b350cec2c71c958
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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