Water → HCID 59643422, compound

HRID 2251564Notes

Reaction equation

HRID 2251564 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.Cl.[NH2:17]O.O>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[O:11][N:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 63319772HCID 63319772, compound

Product 1

HCID 59643422HCID 59643422, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-bromophenyl)-3-cyclopropyl-1,3-propanedione (2.60 g, 9.73 mmol) in anhydrous MeOH (80 ml) was added hydroxylamine hydrochloride (2.71 g, 39.00 mmol). The mixture was heated to reflux for 14 h. Upon cooling, the solution was poured into water, and extracted with CH2Cl2 (3×200 ml). The combined organic phases were dried with MgSO4 and concentrated in vacuo. The regioisomers were separated by flash chromatography (CH2Cl2/hexanes, 10:90 to 40:60) to yield the title compound as a white solid (1.04 g, 40%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 14 h
  3. temperatureUpon cooling
  4. extractionextracted with CH2Cl2 (3×200 ml)
  5. dry with materialThe combined organic phases were dried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe regioisomers were separated by flash chromatography (CH2Cl2/hexanes, 10:90 to 40:60)

Sources & evidence

ORD record
ord-dcf47944b33f43b79c9d3133e374370c
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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