Hydroxyamine hydrochloride → HCID 73504023, compound

HRID 374911Notes

Reaction equation

HRID 374911 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

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 18996097HCID 18996097, compound

Product 1

HCID 73504023HCID 73504023, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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

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

Sources & evidence

ORD record
ord-d67da2777aee4f5bb6c6ba980016d36c
Source dataset
uspto-grants-1996_01
Patent number
US05482966

Reaction notes

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