Hydrogen Bromide → HCID 54311782, compound

HRID 1415950Notes

Reaction equation

HRID 1415950 reaction equation
C([O:8][C:9]1[C:18]([F:19])=[C:17]([F:20])[CH:16]=[C:15]2[C:10]=1[C:11](=[O:40])[C:12]([C:35]([O:37]CC)=[O:36])=[CH:13][N:14]2[C:21]1[C:26]([F:27])=[CH:25][C:24]([F:28])=[C:23]([NH:29]C(OCC)=O)[CH:22]=1)C1C=CC=CC=1.Br>C(O)(=O)C>[NH2:29][C:23]1[CH:22]=[C:21]([N:14]2[C:15]3[C:10](=[C:9]([OH:8])[C:18]([F:19])=[C:17]([F:20])[CH:16]=3)[C:11](=[O:40])[C:12]([C:35]([OH:37])=[O:36])=[CH:13]2)[C:26]([F:27])=[CH:25][C:24]=1[F:28]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 54387038HCID 54387038, compound

Product 1

HCID 54311782HCID 54311782, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 5-benzyloxy-1-(3-ethoxycarbonylamino-4,6-difluorophenyl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (500 mg) was added to 5 ml of 48% hydrobromic acid and 5 ml of acetic acid. The solution was heated at reflux overnight. The reaction solution was allowed to cool down and concentrated in vacua, and ethanol was added to the residue. The solid was collected by filtration and washed with diethyl ether to give 130 mg of the title compound.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux overnight
  3. temperatureto cool down
  4. concentrationconcentrated in vacua, and ethanol
  5. additionwas added to the residue
  6. filtrationThe solid was collected by filtration
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-18c6522576154370a3dcc5cdc66b3aa0
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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