Dichloromethane → HCID 10392180, compound

HRID 1708552Notes

Reaction equation

HRID 1708552 reaction equation
C(Cl)Cl.O1CCCC1.[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([F:21])[C:19]=1[F:20])[N:16]([NH:22][CH3:23])[CH:15]=[C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:13]2=[O:29].[C:30]([O:34][C:35]([C:37](=[CH2:45])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:36])([CH3:33])([CH3:32])[CH3:31]>[Ti](Cl)(Cl)(Cl)Cl.O.C(OCC)(=O)C>[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([F:21])[C:19]=1[F:20])[N:16]([N:22]([CH3:23])[CH2:45][CH:37]([C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:36])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH:15]=[C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:13]2=[O:29]

Participants

8

Reactant 4

HCID 6344Dichloromethane2×HCID 8028TetrahydrofuranHCID 11096368Propanedioic acid, methylene-, bis(1,1-dimethylethyl) esterHCID 11098599Ethyl 6,7,8-trifluoro-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 10392180HCID 10392180, compoundYield 220.4%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methylene chloride solution (0.667 ml) of 1M titanium tetrachloride was gradually added to a solution of methylene chloride (2 ml) and tetrahydrofuran (54.3 μ) containing ethyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro-4-oxoquinoline-3-carboxylate (200 mg), with stirring under ice-cooling, and then tert-butyl 2-tert-butoxycarbonylacrylate (0.228 g) was added thereto and stirred for 10 minutes with ice-cooling and then for 15 hours at room temperature. The mixture was poured into a mixture of ethyl acetate (20 ml) and water (20 ml). The organic layer separated was washed with brine and dried over magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was then triturated with n-hexane. The precipitates were taken out by filtration and dried with air to obtain ethyl 6,7,8-trifluoro-1-[N-methyl-N-{2,2-bis(tert-butoxycarbonyl)ethyl}amino]-1,4-dihydro-4-oxoquinoline-3-carboxylate (775.8 mg) as a pale yellow powder.

Workup

  1. temperaturecooling
  2. stirringstirred for 10 minutes with ice-
  3. temperaturecooling
  4. customThe organic layer separated
  5. washwas washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was then triturated with n-hexane
  9. filtrationThe precipitates were taken out by filtration
  10. customdried with air

Sources & evidence

ORD record
ord-c7235514ddda40b588d44d2822bfce56
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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