Hydroxyamine hydrochloride → HCID 474736, compound

HRID 2297554Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:30])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=O)[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:31])[C:5]([C:32]([OH:34])=[O:33])=[CH:4]1)[CH3:2].Cl.[NH2:36][OH:37]>>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:30])=[C:10]([N:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20](=[N:36][OH:37])[C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:17][CH2:18]3)[CH:11]=2)[C:6](=[O:31])[C:5]([C:32]([OH:34])=[O:33])=[CH:4]1)[CH3:2]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 474729HCID 474729, compound

Product 1

HCID 474736HCID 474736, compound

Procedure

1-Ethyl-6-fluoro-7-{4-[2-hydroxyimino-2-(4-methoxy-phenyl)ethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was prepared from 1-ethyl-6-fluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.47 g, 1 mmole) and hydroxylamine hydrochloride (0.14 g, 2 mol) by a method similar to that described for Example 3 (74% yield). Mp: 221° C. (dec). 1H NMR (DMSO-d6) δ 1.38 (t, 3H, J=7.2), 2.61 and 3.24 (two m, 8H), 3.41 and 3.77 (two s, 2H), 3.78 (s, 3H), 4.56 (q, 2H, J=7.2), 6.93 (m, 2H),7.15 (d, 1H, J=7.6),7.72 (m, 2H), 7.89 (d, 1H, J=13.6), 8.93 (s, 1H), 10.95 and 11.26 (two s, 1H), 15.29 (br s, 1H). Anal. Calcd. for C25H27FN4O5•0.25 H2O: C, 61.66; H, 5.69; N, 11.50. Found: C, 61.61; H, 5.70; N, 11.27.

Sources & evidence

ORD record: ord-72bf86b11903419ea89050ea0c3e573c
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492373B2

Reaction notes

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