Sulfuric Acid → Ethyl 8-chloro-6,7-difluoro-1-(2,4-difluoro-5-nitrophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1415947Notes

Reaction equation

HRID 1415947 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:8]([F:32])=[C:9]([F:31])[CH:10]=[C:11]2[C:16]=1[N:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[F:24])[CH:14]=[C:13]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:12]2=[O:30].[N+:33]([O-])([O-:35])=[O:34].[K+]>>[Cl:6][C:7]1[C:8]([F:32])=[C:9]([F:31])[CH:10]=[C:11]2[C:16]=1[N:15]([C:17]1[CH:22]=[C:21]([N+:33]([O-:35])=[O:34])[C:20]([F:23])=[CH:19][C:18]=1[F:24])[CH:14]=[C:13]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:12]2=[O:30]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 54407716HCID 54407716, compound

Product 1

HCID 54202503Ethyl 8-chloro-6,7-difluoro-1-(2,4-difluoro-5-nitrophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 86.3%

Procedure

To 15 ml of sulfuric acid was added 2.5 g of ethyl 8-chloro-6,7-difluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate. With ice cooling, 950 mg of potassium nitrate was added in portions and the solution was stirred overnight at room temperature. The reaction solution was poured into ice water and stirred overnight at room temperature. The precipitate was collected by filtration and washed with water, ethanol and diethyl ether to give 2.4 g of the title compound.

Workup

  1. stirringstirred overnight at room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-4940cf5798c84ea796dca34576c7010a
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

Loading…