Potassium Iodide → HCID 482671, compound

HRID 2297552Notes

Reaction equation

HRID 2297552 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:20])=[C:10]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:11]=2[F:13])[C:6](=[O:21])[C:5]([C:22]([OH:24])=[O:23])=[CH:4]1)[CH3:2].C(=O)(O)[O-].[Na+].[I-].[K+].Br[CH2:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:35]>CN(C=O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:20])=[C:10]([N:14]3[CH2:15][CH2:16][N:17]([CH2:33][C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:35])[CH2:18][CH2:19]3)[C:11]=2[F:13])[C:6](=[O:21])[C:5]([C:22]([OH:24])=[O:23])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6259Phenacyl bromideHCID 1135233-Quinolinecarboxylic acid, 1,4-dihydro-6,8-difluoro-1-ethyl-4-oxo-7-(1-piperazinyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 482671HCID 482671, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-ethyl-6,8-difluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid ( 0.5 1.48 mmole) [J. B. Cornett et. al., Annu. Rep. Med. Chem., 21, 138 (1986).], sodium bicarbonate (0.12 g, 1.48 mmole), potassium iodide (0.08 g, 0.5 mmole), and 2-bromoacetophenone (0.37 g, 1.86 mmole) in DMF (40 ml) was stirred at room temperature for 3 hr, then poured into ice-water (50 ml), and extracted with CH2Cl2 (50 ml×3). The extract was washed with water, dried over Na2SO4, and evaporated. The residual solid was crystallized from ethanol-chloroform(5:1) to give 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(4-phenacyl-1-piperazinyl)-quinoline-3-carboxylic acid (0.49 g, 73%). Mp: 167° C. (dec). 1H NMR (DMSO-d6) δ1.44 (t, 3H, J=7.0), 2.70 and 3.32 (two m, 8H), 3.97 (s, 2H), 4.59 (q, 2H, J=7.0), 7.54 and 8.02 (m, 5H), 7.85 (d, 1H, J=13.6), 8.92 (s, 1H), 14.95 (br s, 1H). Anal. Calcd. for C24H23F2N3O4•0.5 H2O: C, 62.06; H, 5.21; N, 9.05. Found: C, 62.18; H, 5.09; N, 9.06.

Workup

  1. extractionextracted with CH2Cl2 (50 ml×3)
  2. washThe extract was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residual solid was crystallized from ethanol-chloroform(5:1)

Sources & evidence

ORD record
ord-1ba473a931d149eca71aae03d5de7257
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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