Potassium Nitrate → Ethyl 1-cyclopentyl-6,7-difluoro-8-methoxy-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 561099Notes

Reaction equation

HRID 561099 reaction equation
[CH:1]1([N:6]2[C:15]3[C:10](=[CH:11][C:12]([F:19])=[C:13]([F:18])[C:14]=3[O:16][CH3:17])[C:9](=[O:20])[C:8]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:26]([O-])([O-:28])=[O:27].[K+]>OS(O)(=O)=O>[CH:1]1([N:6]2[C:15]3[C:10](=[C:11]([N+:26]([O-:28])=[O:27])[C:12]([F:19])=[C:13]([F:18])[C:14]=3[O:16][CH3:17])[C:9](=[O:20])[C:8]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 57794160Ethyl 1-cyclopentyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 59003055Ethyl 1-cyclopentyl-6,7-difluoro-8-methoxy-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 15 (6.1 g, 17.4 mmol) in concentrated H2SO4 (60 mL) was treated portionwise at 0° C. with solid KNO3 (2.64 g, 26 mmol). After stirring at 0° C. for 1 h, the reaction mixture was poured into 500 mL of ice-water and the resulting precipitate was removed by filtration, washed with water and dissolved in CH2Cl2. The resulting solution washed with 5% NaHCO3, dried and evaporated to yield 16 as a yellow solid (6.0 g, 87%).

Workup

  1. customthe resulting precipitate was removed by filtration
  2. washwashed with water
  3. dissolutiondissolved in CH2Cl2
  4. washThe resulting solution washed with 5% NaHCO3
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-99d9fd7eeb5b4b75be41820b0292415a
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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