HCID 19807254, compound → HCID 10409570, compound

HRID 1461394Notes

Reaction equation

HRID 1461394 reaction equation
[ClH:1].[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:24])=[C:12]([C:15]4[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([CH2:22]O)[CH:16]=4)[CH:13]=3)[C:8](=[O:25])[C:7]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6]2)[CH2:4][CH2:3]1>S(Cl)(Cl)=O>[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:24])=[C:12]([C:15]4[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([CH2:22][Cl:1])[CH:16]=4)[CH:13]=3)[C:8](=[O:25])[C:7]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:6]2)[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 19807254HCID 19807254, compound

Product 1

HCID 10409570HCID 10409570, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Ethyl 1-cyclopropyl-6-fluoro-7-[2-(hydroxymethyl)-6-methyl-4-pyridinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylate hydrochloride (6.68 g) in 40 ml thionyl chloride was heated at reflux for two hours. The excess thionyl chloride was removed in vacuo and by repeatedly adding ethanol and concentrating. The residue was crystallized from ethanol to give 5.50 g ethyl 1-cyclopropyl-7-[2-(chloromethyl)-6-methyl-4-pyridinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate as its hydrochloride salt.

Workup

  1. temperatureat reflux for two hours
  2. customThe excess thionyl chloride was removed in vacuo and by repeatedly adding ethanol
  3. concentrationconcentrating
  4. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-0fa3c2d361cd4e25bf749ed7e8060bad
Source dataset
uspto-grants-1991_12
Patent number
US05075319

Reaction notes

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