Hydroxyamine hydrochloride → HCID 482674, compound

HRID 2297564Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:30])=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=O)[CH2:16][CH2:15]3)[C:11]=2[F:13])[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:14]3[CH2:15][CH2:16][N:17]([CH2:20][C:21]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)=[N:36][OH:37])[CH2:18][CH2:19]3)[C:11]=2[F:13])[C:6](=[O:31])[C:5]([C:32]([OH:34])=[O:33])=[CH:4]1)[CH3:2]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 10950831HCID 10950831, compound

Product 1

HCID 482674HCID 482674, compound

Procedure

1-Ethyl-6,8-difluoro-7-{4-[2-(4-fluorophenyl)-2-hydroxyiminoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid was prepared from 1-ethyl-6,8-difluoro-7-{4-[2-(4-fluorophenyl)-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 (70% yield). Mp: 201° C. (dec). 1H NMR (DMSO-d6) δ 1.42 (t, 3H, J=7.0), 2.58 and 3.29 (two m, 8H), 3.41 and 3.73 (two s, 2H), 4.57 (q, 2H, J=7.0), 7.44-7.87 (m, 4 H), 7.90 (d, 1H, J=12.0), 8.95 (s, 1H), 11.18 and 11.65 (two s, 1H), 14.92 (br s, 1H). Anal. Calcd. for C24H23F3N4O4•0.5 H2O: C, 57.95; H, 4.86; N, 11.26. Found: C, 57.91; H, 4.83; N, 11.12.

Sources & evidence

ORD record: ord-08e50d33e4544027972e027608f2888c
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492373B2

Reaction notes

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