Hydrogen Bromide → HCID 13745458, compound

HRID 1788662Notes

Reaction equation

HRID 1788662 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]([C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1)[CH:7]=[C:6]([C:21]([O:23]CC)=[O:22])[C:5]2=[O:26].Br>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]([C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)[CH:7]=[C:6]([C:21]([OH:23])=[O:22])[C:5]2=[O:26]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 13745457HCID 13745457, compound

Product 1

HCID 13745458HCID 13745458, compoundYield 92.2%

Procedure

To ethyl 6,7-difluoro-1-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.70 g) is added 48% hydrobromic acid (8 ml), and the mixture is stirred at 100°-110° C. for 3 hour. After cooling, the precipitated crystals are separated by filtration, washed with water and recrystallized from dichloromethane-ethanol to give 6,7-difluoro-1-(4-hydroxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.57 g) as colorless needles, m.p. 288°-290° C.

Workup

  1. temperatureAfter cooling
  2. customthe precipitated crystals are separated by filtration
  3. washwashed with water
  4. customrecrystallized from dichloromethane-ethanol

Sources & evidence

ORD record
ord-64c09d7bf10743029fcdc8099b159fc4
Source dataset
uspto-grants-1987_08
Patent number
US04684648

Reaction notes

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