HCID 178471852, compound → 1-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 1073592Notes

Reaction equation

HRID 1073592 reaction equation
Cl[C:2]1[C:11]([C:12]([C:14](=[CH:20][NH:21][CH:22]2[CH2:24][CH2:23]2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:26])=[C:7]([F:25])[CH:8]=2)[N:3]=1>N12CCCN=C1CCCCC2.C(O)C.O.C(OC(C)C)(C)C>[CH:22]1([N:21]2[C:2]3[N:3]=[C:4]4[CH:5]=[C:6]([F:26])[C:7]([F:25])=[CH:8][C:9]4=[CH:10][C:11]=3[C:12](=[O:13])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20]2)[CH2:24][CH2:23]1

Participants

6

Reactant 1

HCID 178471852HCID 178471852, compound

Product 1

HCID 148533401-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 74.9%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 7914Diisopropyl EtherSolventHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Conditions

Temperature
20 °C

Procedure

A stirred suspension of 5.27 g of ethyl 2-(2-chloro-6,7-difluoro quinoline-3-carbonyl)-3-cyclopropylaminoacrylate in 2.22 g of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 120 cm3 of ethanol is heated at a temperature close to 75° C. for 35 minutes. After cooling to about 20° C., the reaction mixture is taken up in 100 cm3 of water and extracted with once 100 cm3 and twice 50 cm3 of trichloromethane. The combined organic extracts are washed with 3 times 50 cm3 of water, dried over magnesium sulphate, filtered and concentrated under reduced pressure (20 kPa) at a temperature close to 20° C. The dry extract obtained is taken up in 30 cm3 of diisopropyl ether, drained and recrystallized from a mixture of 75 cm3 of ethanol and 75 cm3 of dimethylformamide. 3.57 g of 1 -cyclopropyl-3-ethoxycarbonyl-7,8-di fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a yellow solid melting at 229°-230° C.

Workup

  1. temperatureis heated at a temperature
  2. customclose to 75° C. for 35 minutes
  3. extractionextracted with once 100 cm3 and twice 50 cm3 of trichloromethane
  4. washThe combined organic extracts are washed with 3 times 50 cm3 of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (20 kPa) at a temperature
  8. customclose to 20° C
  9. extractionThe dry extract
  10. customobtained
  11. customrecrystallized from a mixture of 75 cm3 of ethanol and 75 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-c21079e50d524d68a6ce93cfaee19cc5
Source dataset
uspto-grants-1990_11
Patent number
US04970213

Reaction notes

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