Hydroxyamine hydrochloride → HCID 86585219, compound

HRID 2297562Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:29])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)=[O:21])[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:30])[C:5]([C:31]([OH:33])=[O:32])=[CH:4]1)[CH3:2].Cl.[NH2:35]O>>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:29])=[C:10]([N:13]3[CH2:14][CH2:15][N:16]([C:19](=[NH:35])[CH:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[OH:21])[CH2:17][CH2:18]3)[CH:11]=2)[C:6](=[O:30])[C:5]([C:31]([OH:33])=[O:32])=[CH:4]1)[CH3:2]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 482669HCID 482669, compound

Product 1

HCID 86585219HCID 86585219, compound

Procedure

1-Ethyl-6-fluoro-7-{4-[2-(4-chlorophenyl)-2-hydroxy-iminoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid was prepared from 1-ethyl-6-fluoro-7-{4-[2-(4-chlorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (0.24 g, 0.5 mmole) and hydroxylamine hydrochloride (0.07 g, 1 mmol) by a method similar to that described for Example 3 (73% yield). 1H NMR (DMSO-d6) δ 1.39 (t, 3H, J=7.0), 2.61 and 3.24 (two m, 8H), 3.44 and 3.73 (two s, 2H), 4.56 (q, 2H, J=7.0), 7.24 and 7.78 (two m, 5H), 7.89 (d, 1H, J=13.4), 8.93 (s, 1H), 11.03 and 11.49 (two s, 1 H), 15.35 (br s, 1H). Anal. Calcd. for C24H24FClN4O4•0.25 H2O: C, 58.66; H, 5.02; N, 11.40. Found: C, 58.48; H, 5.01; N, 11.29.

Sources & evidence

ORD record: ord-759a83c668c447ad8b1e9e45914c6c8d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492373B2

Reaction notes

Loading…