Hydroxyamine hydrochloride → HCID 21763498, compound

HRID 1808147Notes

Reaction equation

HRID 1808147 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)=[CH:2]1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[K+]>C(O)C.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:20][OH:21])=[CH:2]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 12348663HCID 12348663, compound

Product 1

HCID 21763498HCID 21763498, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

2-(1H-indol-3-yl)-1-phenylethanone (0.97 g, 4.12 mmol) dissolved in absolute ethanol (20 ml) was added to a solution of hydroxylamine hydrochloride (0.97 g, 13.95 mmol) and potassium acetate (1.54 g, 15.74 mmol) in absolute ethanol (20 ml). This reaction mixture was stirred for 24 h at room temperature. The batch was then boiled for 3 h with reflux. The batch was then dissolved in water (20 ml) at 70° C. The batch was then left to stand for 5 h at 4° C. Since no solid separated out, the volatile constituents were removed completely in a vacuum. The residue was mixed with water (10 ml) and the pH value of the solution adjusted to pH 11 with 5N sodium hydroxide solution. The mixture was then extracted with ethyl acetate (5×30 ml). The combined organic phases were dried with sodium sulphate, filtered and all the volatile constituents removed in a vacuum. Yield: 90% (990 mg) yellow-brown oil

Workup

  1. waitThe batch was then boiled for 3 h
  2. temperaturewith reflux
  3. waitThe batch was then left
  4. waitto stand for 5 h at 4° C
  5. customSince no solid separated out
  6. customthe volatile constituents were removed completely in a vacuum
  7. additionThe residue was mixed with water (10 ml)
  8. extractionThe mixture was then extracted with ethyl acetate (5×30 ml)
  9. dry with materialThe combined organic phases were dried with sodium sulphate
  10. filtrationfiltered
  11. customall the volatile constituents removed in a vacuum

Sources & evidence

ORD record
ord-334571bad9f340a0b414f148f55a0856
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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