Dichloromethane → HCID 73197256, compound

HRID 2297550Notes

Reaction equation

HRID 2297550 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:23])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20](=O)[CH3:21])[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:24])[C:5]([C:25]([OH:27])=[O:26])=[CH:4]1)[CH3:2].Cl.[NH2:29][OH:30].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:23])=[C:10]([N:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20](=[N:29][OH:30])[CH3:21])[CH2:17][CH2:18]3)[CH:11]=2)[C:6](=[O:24])[C:5]([C:25]([OH:27])=[O:26])=[CH:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 136887983-Quinolinecarboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(4-(2-oxopropyl)-1-piperazinyl)-

Product 1

HCID 73197256HCID 73197256, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of the 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-oxopropyl)-1-piperazinyl]-quinoline-3-carboxylic acid [H. Kondo et. al., J. Med. Chem., 29, 2020 (1986)] (0.38 g, 1 mmol) 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 stirred for 20 hr at room temperature, then 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-7-[4-(2-hydroxyiminopropyl)-1-piperazinyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid as an off-white amorphous solid (0.28 g, 72%). Mp: 218° C. (dec). 1H NMR (DMSO-d6) δ1.41 (t, 3H, J=7.2), 1.81 (s, 3H), 2.54 (m, 4H), 3.03 (s, 2H2), 3.33 (m, 4H), 4.57 (q, 2H, J=7.2), 7.17 (d, H, J=7.2), 7.90 (d, 1H, J=13.6), 8.92 (s, 1H), 10,61 (s, 1H), 15.27 (br s, 1H). Anal. Calcd. for C19H23FN4O4•0.5 H2O: C, 57.14; H. 6.06; N, 14.03. Found: C, 57.43; H, 5.87; N, 13.83.

Workup

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

Sources & evidence

ORD record
ord-99d944ade6464483945c06a61fde8aa3
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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