Dichloromethane → HCID 482680, compound

HRID 2297551Notes

Reaction equation

HRID 2297551 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:28])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=O)[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:29])[C:5]([C:30]([OH:32])=[O:31])=[CH:4]1)[CH3:2].Cl.[NH2:34][OH:35].C(=O)(O)[O-].[Na+].C(Cl)Cl>CO.O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:28])=[C:10]([N:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20](=[N:34][OH:35])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17][CH2:18]3)[CH:11]=2)[C:6](=[O:29])[C:5]([C:30]([OH:32])=[O:31])=[CH:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 443297Hydroxyamine hydrochlorideHCID 482668HCID 482668, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 482680HCID 482680, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-phenacyl-1-piperazinyl)-quinoline-3-carboxylic acid (0.44 g, 1 mmole) [H. Kondo et. al., J. Med. Chem., 29, 2020 (1986)] in absolute methanol (20 ml) was added a solution of hydroxylamine hydrochloride (0.14 g, 2 mmol) and sodium bicarbonate (0.17 g, 2 mmol) in water (2 ml). The mixture was heated at reflux for 36 hr and allowed to cool to room temperature. CH2Cl2 (50 ml) was added, and the layers were separated. The organic phase was washed successively with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to give a solid which was purified by flash column chromatography (silica gel, with CH2Cl2/methanol (10:1) as the eluant) and crystillization from CH2Cl2/methanol (5:1) to give 1-ethyl-6-fluoro-4-oxo-7-[4-(2-hydroxyimino-2-phenylethyl)-1-piperazinyl]-1,4-dihydroquinoline-3-carboxylic acid as an off-white amorphous solid (0.31 g, 68%). Mp: 203° C. (dec). 1H NMR (DMSO-d6) δ 1.38 (t, 3H, J=7.2), 2.64 and 3.25 (two m, 8H), 3.43 and 3.73 (two s, 2 H), 4.56 (q, 2H, J=7.2), 7.15 (d, 1H, J=7.2), 7.36-7.79 (m, 5H), 7.88 (d, 1H, J=13.2), 8.92 (s, 1H), 10.99 and 11.48 (two s, 1H), 15.07 (br s, 1H). Anal. Calcd. for C24H25FN4O4•1.5 H2O: C, 60.10; H, 5.89; N, 11.68. Found: C, 60.19; H, 5.81; N, 11.64.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 36 hr
  3. customthe layers were separated
  4. washThe organic phase was washed successively with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a solid which
  9. customwas purified by flash column chromatography (silica gel

Sources & evidence

ORD record
ord-c00a9a79fc5e482197b633402d69e44f
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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