Potassium Carbonate → Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1078276Notes

Reaction equation

HRID 1078276 reaction equation
[CH:1]1([NH:4][CH:5]=[C:6]([C:12](=[O:26])[C:13]2[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([F:22])[C:16]([F:23])=[C:15]([CH3:24])[C:14]=2F)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C1OCCOCCOCCOCCOCCOC1>[CH:1]1([N:4]2[C:14]3[C:13](=[C:18]([N+:19]([O-:21])=[O:20])[C:17]([F:22])=[C:16]([F:23])[C:15]=3[CH3:24])[C:12](=[O:26])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178471886HCID 178471886, compound

Product 1

HCID 10736705Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-5-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 90.5%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10.0 g of ethyl 3-cyclopropylamino-2-(2,4,5-trifluoro-3-methyl-6-nitrobenzoyl)acrylate and 0.1 g of 18-crown-6-ether in 100 ml of tetrahydrofuran, 8.04 g of potassium carbonate was added, and then the mixture was stirred at room temperature for 23 hours. The deposited crystals were collected by filtration and washed with tetrahydrofuran, water and acetone to give 8.56 g of the desired compound. Recrystallization from N,N-dimethylformamide gave colorless needles, which were identified as the compound of Example 5.

Workup

  1. filtrationThe deposited crystals were collected by filtration
  2. washwashed with tetrahydrofuran, water and acetone

Sources & evidence

ORD record
ord-8209374f09dd42d088033ae6ba1fab9f
Source dataset
uspto-grants-1996_08
Patent number
US05547962

Reaction notes

Loading…