Hydroxyamine hydrochloride → HCID 482696, compound

HRID 2297558Notes

Reaction equation

HRID 2297558 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:37])=[C:17]([N:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]([C:29]5[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=5)=O)[CH2:22][CH2:21]4)[CH:18]=3)[C:13](=[O:38])[C:12]([C:39]([OH:41])=[O:40])=[CH:11]2)=[C:6]([F:42])[CH:5]=1)([O-:3])=[O:2].Cl.[NH2:44][OH:45].C(=O)(O)[O-].[Na+].C(Cl)Cl.CO>C(O)C.O.C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:37])=[C:17]([N:20]4[CH2:21][CH2:22][N:23]([CH2:26][C:27](=[N:44][OH:45])[C:29]5[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=5)[CH2:24][CH2:25]4)[CH:18]=3)[C:13](=[O:38])[C:12]([C:39]([OH:41])=[O:40])=[CH:11]2)=[C:6]([F:42])[CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 482688HCID 482688, compoundHCID 516892Sodium BicarbonateHCID 21226129Dichloromethane methanol2×

Product 1

HCID 482696HCID 482696, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the 1-(4-nitro-2-fluorophenyl)-6-fluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.58 g, 1 mmol) in absolute ethanol (20 ml) were added hydroxylamine hydrochloride (0.14 g, 2 mmol) and sodium bicarbonate (0.17 g, 2 mmol) dissolved in distilled water (2 ml). The reaction mixture was refluxed for 20 hr, then diluted with CH2Cl2 (50 ml). The organic phase was washed successively with water and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a pale yellow 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-(4-nitro-2-fluorophenyl)-6-fluoro-7-{4-[2-hydroxyimino-2-(4-methoxy-phenyl)ethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.46 g, 80% yield). Mp: 216° C. (dec). 1H NMR (DMSO-d6) δ 2.54 and 3.02 (two n, 8H), 3.63 (s, 2H), 3.76 (s, 3H), 6.36 (d, 1H, J=6.8), 6.89 (d, 2H, J=8.8), 7.67 (d, 2H, J=8.8), 7.98 (d, 1H, J=13.2), 8.12-8.53 (m, 3H) 8.91 (s, 1H), 11.22 (s, 1H), 14.85 (br s, 1H) . Anal. Calcd. for C29H,5F2N5O7•2.5 H2O: C, 54.55; H, 4.74; N, 10.97. Found: C, 54.19; H, 4.36; N, 10.66.

Workup

  1. temperatureThe reaction mixture was refluxed for 20 hr
  2. washThe organic phase was washed successively with water and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a pale yellow solid which
  7. customwas purified by flash column chromatography (silica gel

Sources & evidence

ORD record
ord-816cad714600409fb83906bcfa78bc1b
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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