HCID 20083118, compound → HCID 20083112, compound

HRID 1708538Notes

Reaction equation

HRID 1708538 reaction equation
C(O[C:6]([N:8]([N:10]1[C:19]2[C:14](=[C:15]([F:23])[C:16]([F:22])=[C:17]([F:21])[C:18]=2[F:20])[C:13](=[O:24])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:11]1)C)=O)(C)(C)C.Cl.O1CCOCC1>C(OCC)(=O)C>[CH3:6][NH:8][N:10]1[C:19]2[C:14](=[C:15]([F:23])[C:16]([F:22])=[C:17]([F:21])[C:18]=2[F:20])[C:13](=[O:24])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:11]1

Participants

4

Reactant 2

HCID 20083118HCID 20083118, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 20083112HCID 20083112, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 1-(N-tert-butoxycarbonyl-N-methylamino)-5,6,7,8-tetrafluoro -1,4-dihydro-4-oxoquinoline-3-carboxylate (4.2 g) was dissolved in ethyl acetate (30 ml),. 4N hydrochloric acid-dioxane solution (40 ml) was added thereto with ice-cooling and stirred overnight at room temperature, and the solvent was removed by distillation. The residue was dissolved in chloroform (100 ml), and 10% sodium carbonate aqueous solution (50 ml) was added thereto and stirred for 30 minutes at room temperature. The organic layer was separated out and dried over magnesium sulfate, and the solvent was removed by distillation. The crystals were dispersed in ether and filtered out to obtain ethyl 1-methylamino-5,6,7,8-tetrafluoro -1,4-dihydro-4-oxoquinoline-3-carboxylate (2.9 g).

Workup

  1. temperaturewith ice-cooling
  2. customthe solvent was removed by distillation
  3. dissolutionThe residue was dissolved in chloroform (100 ml)
  4. addition10% sodium carbonate aqueous solution (50 ml) was added
  5. stirringstirred for 30 minutes at room temperature
  6. customThe organic layer was separated out
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was removed by distillation
  9. additionThe crystals were dispersed in ether
  10. filtrationfiltered out

Sources & evidence

ORD record
ord-283fe275162344f5927eac42d893aad7
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

Loading…