Hydroxyamine hydrochloride → HCID 136388571, compound

HRID 395312Notes

Reaction equation

HRID 395312 reaction equation
[C:1]([C:4]1[C:14]([OH:15])=[CH:13][C:12]2[CH:11]3[CH2:16][CH:7]([CH2:8][N:9]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:10]3)[C:6]=2[CH:5]=1)(=O)[CH3:2].Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>CO.O>[F:20][C:18]([F:21])([F:19])[C:17]([N:9]1[CH2:10][CH:11]2[CH2:16][CH:7]([C:6]3[CH:5]=[C:4]([C:1](=[N:24][OH:25])[CH3:2])[C:14]([OH:15])=[CH:13][C:12]=32)[CH2:8]1)=[O:22]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 218647091-(4-Acetyl-5-hydroxy-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone

Product 1

HCID 136388571HCID 136388571, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

1-(4-Acetyl-5-hydroxy-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (190 mg, 0.605 mmol), hydroxylamine HCl (99 mg, 1.21 mmol) and sodium acetate (118 mg, 1.21 mmol) were combined in methanol (4 mL) and H2O (1 mL) and warmed to 65° C. for 18 hours. The mixture was cooled, diluted with H2O and extracted with ethyl acetate which was dried (Na2SO4), filtered and concentrated to provide a yellow oil (177 mg, 93%).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate which
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf5f31bf4cbb4e029144223b84bca36d
Source dataset
uspto-grants-2003_08
Patent number
US06605610B1

Reaction notes

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