Water → HCID 86615498, compound

HRID 2197895Notes

Reaction equation

HRID 2197895 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH3:12])=[CH:7][CH:6]=1.Cl.[NH2:20][OH:21].O>C(O)C>[NH2:1][C:2]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[N:20][OH:21])[CH3:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 68459270HCID 68459270, compound

Product 1

HCID 86615498HCID 86615498, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To the product from Example 163a (150 mg, 0.57 mmol) in ethanol (15 mL) was added hydroxylamine hydrochloride (41.8 mg, 0.60 mmol), and disopropylethylamine (82 mg, 0.63 mmol). The reaction was heated at 60° C. for 3 h. The reaction was cooled and poured into water. The solution was extracted with ethyl ether. The organic layer washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (65 mg, 42%).

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe solution was extracted with ethyl ether
  3. washThe organic layer washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cef8a9fd4fa8452d9f2aace3abe86948
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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