Water → 5-{4-Hydroxy-2-[4-(2-piperidin-1-ylethoxy)phenylamino]phenyl}indan-1-one oxime

HRID 1434095Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=O)[CH2:12][CH2:11]3)=[C:4]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=2)[CH:3]=1.[Cl-].[OH:35][NH3+:36].N1C=CC=CC=1.O>C(O)C.O1CCCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[N:36][OH:35])[CH2:12][CH2:11]3)=[C:4]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]3)=[CH:21][CH:20]=2)[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-{4-hydroxy-2-[4-(2-piperidin-1-ylethoxy)phenylamino]phenyl}indan-1-one (28 mg) in ethanol (1 ml) and tetrahydrofuran (0.2 ml) were sequentially added hydroxylammonium chloride (43 mg) and pyridine (0.2 ml), and the solution was stirred overnight at 60° C. Water was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system) to provide the title compound (6 mg).

Workup

stirringby stirring
extractionthe solution was extracted with ethyl acetate
washsequentially washed with water and brine
customthe solvent was evaporated in vacuo
customThe residue was purified by NH silica gel column chromatography (ethyl acetate-methanol system)

Sources & evidence

ORD record: ord-ce5f1912bd6d459896b8a1ca0e693bae
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612114B2

Reaction notes

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