Hydroxyamine hydrochloride → HCID 73504023, compound

HRID 1729359Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:20]2([O:26][CH3:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:5]=[C:6]([S:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13](=O)[CH2:14][CH2:15][O:16]3)=[CH:11][CH:10]=2)[CH:7]=1.Cl.[NH2:29][OH:30]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:20]2([O:26][CH3:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:5]=[C:6]([S:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13](=[N:29][OH:30])[CH2:14][CH2:15][O:16]3)=[CH:11][CH:10]=2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-[5-fluoro-3-(4-methoxytetrahydropyran-4-yl)phenylthio]chroman-4-one (0.172 g), hydroxylamine hydrochloride (0.04 g) and pyridine (3 ml) was stirred and heated to 80° C. for 2 hours. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and dilute aqueous hydrochloric acid. The organic phase was washed with brine, dried (MgSO4) and evaporated. The product was purified by column chromatography using a 4:1 mixture of petroleum ether and ethyl acetate as eluent. There was thus obtained, as a mixture of (E)- and (Z)-isomers, 7-[5-fluoro-3-(4-methoxytetrahydropyran-4-yl)phenylthio]chroman-4-one oxime (0.112 g, 63%), m.p. 173°-174° C.;

Workup

temperatureThe mixture was cooled to ambient temperature
custompartitioned between ethyl acetate and dilute aqueous hydrochloric acid
washThe organic phase was washed with brine
dry with materialdried (MgSO4)
customevaporated
customThe product was purified by column chromatography
additiona 4:1 mixture of petroleum ether and ethyl acetate as eluent

Sources & evidence

ORD record: ord-bd79d42b0e4345fbb9cf99c825dbef87
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05332757

Reaction notes

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