Isopropyl iodide → HCID 59002975, compound

HRID 561164Notes

Reaction equation

HRID 561164 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:17]([O-:19])=[O:18])[C:10]([F:16])=[C:11]([F:15])[C:12]=3[OH:14])[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.I[CH:27]([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:17]([O-:19])=[O:18])[C:10]([F:16])=[C:11]([F:15])[C:12]=3[O:14][CH:27]([CH3:29])[CH3:28])[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 59002972HCID 59002972, compound

Product 1

HCID 59002975HCID 59002975, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-5-nitro-4-oxoquinoline-3-carboxylate (393 mg, 1.11 mmol), 2-Iodopropane (0.167 mL, 1.67 mmol) and K2CO3 (231 mg, 1.67 mmol) in DMF (5 mL) was stirred at 80° C. for 5 h. After the reaction mixture was poured into ice-water, the crude product was extracted with CH2Cl2, washed with 1M HCl, saturated aq. NaHCO3 and brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product washed with hot EtOH and dried to yield ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-isopropoxy-5-nitro-4-oxoquinoline-3-carboxylate (237 mg, 54%) as a pale yellow solid.

Workup

  1. extractionthe crude product was extracted with CH2Cl2
  2. washwashed with 1M HCl, saturated aq. NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. washThe crude product washed with hot EtOH
  6. customdried

Sources & evidence

ORD record
ord-ffdf13ea80e449c69176c1a58261b59c
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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