Nitromethane → HCID 53995380, compound

HRID 964537Notes

Reaction equation

HRID 964537 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3F)[C:7](=[O:17])[C:6]([C:18](O)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.C1N=CN([C:26](N2C=NC=C2)=[O:27])C=1.[N+:33]([CH3:36])([O-:35])=[O:34].[H-].[Na+]>C1COCC1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[C:12]=3[O:27][CH3:26])[C:7](=[O:17])[C:6]([C:18](=[O:19])[CH2:36][N+:33]([O-:35])=[O:34])=[CH:5]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 53995380HCID 53995380, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

566 mg of 1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and 648 mg of CDI were put into 20 ml of THF and the mixture solution is stirred under reflux for 24 hours (A solution). 366 mg of nitromethane was mixed in 5 ml of THF and 240 mg of 60% NaH added thereto. The mixture solution was stirred for 24 hours at room temperature and the above A solution was added thereto. The resulting solution was stirred under reflux for 14 hours. The reaction mixture was cooled and the solvent was evaporated under reduced pressure. The produced residue was purified by column chromatography (nucleic acid: ethylacetate =5 : 1) to give 450 mg of the above title compound (yield: 69%).

Workup

  1. temperatureunder reflux for 24 hours (A solution)
  2. stirringThe mixture solution was stirred for 24 hours at room temperature
  3. additionthe above A solution was added
  4. stirringThe resulting solution was stirred
  5. temperatureunder reflux for 14 hours
  6. temperatureThe reaction mixture was cooled
  7. customthe solvent was evaporated under reduced pressure
  8. customThe produced residue was purified by column chromatography (nucleic acid: ethylacetate =5 : 1)

Sources & evidence

ORD record
ord-b84d1bfa70454a6aa49528643e83602e
Source dataset
uspto-grants-1998_06
Patent number
US05770597

Reaction notes

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