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

HRID 1084390Notes

Reaction equation

HRID 1084390 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>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

5

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 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A stirred suspension of 5.27 g of ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-cyclopropylaminoacrylate in 2.22 g of 1,8-diazobicyclo[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 once with 100 cm3 and twice with 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-difluoro-4-oxo-1,4-dihydrobenzo[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 once with 100 cm3 and twice with 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-afc30c8006664bbea4602f174887dc35
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

Loading…