Hydrochloric Acid → HCID 15729406, compound

HRID 373517Notes

Reaction equation

HRID 373517 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9](F)[C:10]([F:15])=[C:11]([F:14])[CH:12]=3)[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.ClC=C(Cl)Cl.Cl>O>[CH2:23]([NH:30][C:9]1[C:10]([F:15])=[C:11]([F:14])[CH:12]=[C:13]2[C:8]=1[C:7](=[O:17])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5][N:4]2[CH:1]1[CH2:3][CH2:2]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6575TrichloroethyleneHCID 7504BenzylamineHCID 14880201Ethyl 1-cyclopropyl-5,6,7-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 15729406HCID 15729406, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.57 g of ethyl 1-cyclopropyl-5,6,7-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, 1.8 ml of benzylamine and 180 ml of trichloroethylene was heated under reflux for 3 hours and 40 minutes. Water and 10% hydrochloric acid were added to the reaction mixture to render the aqueous layer acidic. The trichloroethylene layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was separated and purified by silica gel column chromatography to give 2.78 g of ethyl 5-benzylamino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxlate. m.p. 144°-145° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours and 40 minutes
  3. customThe trichloroethylene layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9c55bd32400546409b3fb1ea35f77d97
Source dataset
uspto-grants-1992_11
Patent number
US05164392

Reaction notes

Loading…