Hydroxylamine → HCID 86595271, compound

HRID 1788367Notes

Reaction equation

HRID 1788367 reaction equation
[NH2:1][OH:2].[CH3:3][C:4]1[CH:13]=[C:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH:25]=[CH:26][CH:27]=[C:28]3[CH2:33][CH2:32][S:31][CH2:30][CH2:29]3)(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1>O1CCCC1>[CH3:3][C:4]1[CH:13]=[C:12]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH2:25][CH:26]([NH:1][OH:2])[CH:27]=[C:28]3[CH2:33][CH2:32][S:31][CH2:30][CH2:29]3)(=[O:23])=[O:24])=[CH:20][CH:21]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86595272HCID 86595272, compound

Product 1

HCID 86595271HCID 86595271, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 50% aqueous solution of hydroxylamine (2 mL) was added to a solution of 0.18 g (0.40 mmol) of 2-methyl-4-{4-[3-(tetrahydrothiopyran-4-ylidene)-1-propene-1-sulfonyl]phenoxymethyl}quinoline obtained in the same manner as Example 9 (9-1) and (9-2) in tetrahydrofuran (5 mL) at room temperature and stirred for 54 hours. After the reaction was completed, the solvent was removed under a reduced pressure, the residue was extracted with chloroform, and the organic layer was dried over magnesium sulfate. After drying, the solution was filtered and the filtrate was concentrated under a reduced pressure, and the obtained residue was subjected to column chromatography on silica gel (silica gel 4 g, developing solvent; chloroform:methanol=20:1) to obtain 0.12 g (yield 63%) of N-{2-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]-1-(tetrahydrothiopyran-4-ylidenemethyl)ethyl}hydroxylamine (III-17) as a white crystal. Its physical properties are shown below.

Workup

  1. customthe solvent was removed under a reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customAfter drying
  5. filtrationthe solution was filtered
  6. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-c395ebc825df4d51a40a760d2f9d553a
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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