Hydroxylamine → HCID 86668411, compound

HRID 623344Notes

Reaction equation

HRID 623344 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH3:14])([CH3:13])[CH:11]=O)=[CH:9][C:4]=2[O:3][CH2:2]1.[NH2:15][OH:16].N1C=CC=CC=1>C(O)C.Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([CH3:14])([CH3:13])[CH:11]=[N:15][OH:16])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 1049PyridineHCID 82125639HCID 82125639, compound

Product 1

HCID 86668411HCID 86668411, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of Compound I (511 mg, 2.66 mmol) in ethanol (1 mL), HCl.NH2OH (277 mg, 4.00 mmol) and pyridine (2.2 mL, 26.58 mmol) were added and it was stirred at room temperature for 1.5 hours. The reaction mixture was evaporated to dryness and added 10 mL of ethyl acetate. The organic layer was washed with distilled water, dried over anhydrous sodium sulfate, filtered and evaporated. The crude reaction mixture was purified over silica gel column using 5:1 petroleum ether-ethyl acetate as solvent to afford Compound J (528 mg, 96%) as a white foam.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionadded 10 mL of ethyl acetate
  3. washThe organic layer was washed with distilled water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude reaction mixture
  8. customwas purified over silica gel column

Sources & evidence

ORD record
ord-57992066f6af43bf8b39aea593033e98
Source dataset
uspto-grants-2016_04
Patent number
US09302967B2

Reaction notes

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