Sodium Fluoride → Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 330083Notes

Reaction equation

HRID 330083 reaction equation
F[C:2]1[C:20]([CH3:21])=[C:19]([F:22])[C:18]([F:23])=[CH:17][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH:14]1[CH2:16][CH2:15]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[F-].[Na+]>CN(C=O)C>[CH:14]1([N:13]2[C:2]3[C:3](=[CH:17][C:18]([F:23])=[C:19]([F:22])[C:20]=3[CH3:21])[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]2)[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 5235Sodium FluorideHCID 178471874HCID 178471874, compound

Product 1

HCID 9839540Ethyl 1-cyclopropyl-6,7-difluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 2-(2,4,5-trifluoro-3-methylbenzoyl)-3-cyclopropylaminoacrylate (300 mg) and sodium fluoride (70 mg) in anhydrous DMF (2 ml) was stirred at 130° to 140° C. for 6 hours. To the reacting mixture was added ice-water (3 ml), the resulting precipitate was collected by filtration, washed with water and recrystallized from methanol to give the title compound (220 mg) as white needles, mp 220°-221° C.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2c9c953669504a188959aab34584b132
Source dataset
uspto-grants-1990_01
Patent number
US04894458

Reaction notes

Loading…