Pyridine → HCID 154041398, compound

HRID 1885039Notes

Reaction equation

HRID 1885039 reaction equation
[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[C:10]2/[C:11](=O)[CH2:12][CH2:13][C:14]3[C:19]/2=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.[NH2:24][OH:25].N1C=CC=CC=1>ClCCl>[CH3:1][S:2]([C:5]1[CH:22]=[CH:21][C:8]([CH:9]=[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12]/[C:11]/2=[N:24]\[OH:25])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 9879787HCID 9879787, compound

Product 1

HCID 154041398HCID 154041398, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-1-(4-methanesulfonyl-benzylidene)-3,4-dihydro-1H-naphthalene-2-one (50 mg, 0.16 mmol) and hydroxylamine hydrochloride salt (22 mg, 0.32 mmol) was added into pyridine (2.0 ml) and then stirred overnight at reflux condition. Cooled to room temperature, dichloromethane (40 ml) was added, washed twice using 2 N hydrochloric acid (40 ml) and again washed twice using the saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was made to solid by adding diisopropylether and n-hexane, filtrated and dried. As a result, 36.7 mg of the present compound (productive yield 70%) was obtained as a white solid.

Workup

  1. temperatureat reflux condition
  2. washwashed twice
  3. washagain washed twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionby adding diisopropylether and n-hexane
  7. filtrationfiltrated
  8. customdried

Sources & evidence

ORD record
ord-5c71bb88438c4d1db4b8e2ffc50017fe
Source dataset
uspto-grants-2004_07
Patent number
US06768019B2

Reaction notes

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