Water → HCID 73782333, compound

HRID 2186057Notes

Reaction equation

HRID 2186057 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.Cl.[OH:15][NH2:16].C(=O)(O)[O-].[Na+].O>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[N:16][OH:15])[CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 777857-Methoxy-2-tetraloneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 73782333HCID 73782333, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-methoxy-2-tetralone (0.50 g, 2.8 mmol), hydroxyl amine hydrochloride (0.38 g, 5.6 mmol) and sodium bicarbonate (0.47 g, 5.6 mmol) in methanol (20 mL) was heated to reflux for 3 h. The mixture was poured into water (15 mL) and extracted with chloroform. The organic phases were combined, washed with brine, and concentrated to give a white solid. Precipitation from ethyl acetate/hexane gave the title compound (420 mg, 79%) as a granular solid. MS(ES) m/e 191 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with chloroform
  4. washwashed with brine
  5. concentrationconcentrated
  6. customto give a white solid
  7. customPrecipitation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-17e98f2b7f3846c6b8d2e9790a472fc0
Source dataset
uspto-grants-2002_06
Patent number
US06403578B1

Reaction notes

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