Hydroxyamine hydrochloride → HCID 85554874, compound

HRID 569069Notes

Reaction equation

HRID 569069 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)(=O)[CH3:2].Cl.[OH:14][NH2:15]>N1C=CC=CC=1.C(O)C>[C:1](=[N:15][OH:14])([C:4]1[CH:5]=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 128854941-(Thieno[3,2-b]pyridin-6-yl)ethan-1-one

Product 1

HCID 85554874HCID 85554874, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-acetylthieno[3,2-b]pyridine (3.78 g, 21.3 mmol) in pyridine (40 ml) and ethanol (40 ml), under a nitrogen atmosphere, was added hydroxyl amine hydrochloride (5.0 g, 72 mmol). After the reaction mixture was heated at 80° C. for three hours, the solvents were removed under reduced pressure on a rotary evaporator and the residue was diluted with ice water to give crystalline product. This solid was collected by filtration and dissolved in ethyl acetate/methanol, dried over anhydrous sodium sulfate and filtered through charcoal. The solvents were evaporated to give pure product (3.15 g, 77% yield) which was used as is. A small portion was recrystallized from methanol for microanalysis, m.p 210°-213° C.

Workup

  1. customthe solvents were removed under reduced pressure on a rotary evaporator
  2. additionthe residue was diluted with ice water
  3. customto give crystalline product
  4. filtrationThis solid was collected by filtration
  5. dissolutiondissolved in ethyl acetate/methanol
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered through charcoal
  8. customThe solvents were evaporated

Sources & evidence

ORD record
ord-bc81001fd55840cdae93b78c9390f861
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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