Hydroxyamine hydrochloride → HCID 73516783, compound

HRID 482149Notes

Reaction equation

HRID 482149 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:13]3[CH2:17][CH2:16][C:15](=O)[CH:14]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.Cl.[NH2:22][OH:23]>>[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[C:9]([C:13]3[CH2:17][CH2:16][C:15](=[N:22][OH:23])[CH:14]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19065571HCID 19065571, compound

Product 1

HCID 73516783HCID 73516783, compoundYield 113.6%

Procedure

To a stirred solution of 3-[3-(4-fluorophenoxy)phenyl]-2-cyclopentenone (10 g; 0.0373M) in ethanol-pyridine (75 ml-21 ml) was added hydroxylamine hydrochloride (3.37 g; 0.0485M) at room temperature. After stirring for 4 hrs, solvent was removed. To the residue was added dilute aqueous HCl (100 ml), and the whole was extracted with ethyl acetate (200 ml×1, 100 ml×1). The combined organic layers were washed with water (100 ml), brine (100 ml), dried over MgSO4, and concentrated in vacuo to give 12 g of crude subtitle compound [E] as a brown oil, which was used without further purification.

Workup

  1. customsolvent was removed
  2. additionTo the residue was added dilute aqueous HCl (100 ml)
  3. extractionthe whole was extracted with ethyl acetate (200 ml×1, 100 ml×1)
  4. washThe combined organic layers were washed with water (100 ml), brine (100 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83e7addb87c64214b6be58776e2478cc
Source dataset
uspto-grants-1998_08
Patent number
US05792882

Reaction notes

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