Hydroxyamine hydrochloride → HCID 86753867, compound

HRID 1418150Notes

Reaction equation

HRID 1418150 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[NH2:15])=[CH:10][C:9]=1[NH:17][C:18](=[O:36])[CH2:19][CH:20]([C:26]1[CH:31]=[CH:30][C:29](C=O)=[CH:28][C:27]=1[O:34][CH3:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH3:7])([CH3:6])[CH3:5]>N1C=CC=CC=1.O>[C:4]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[NH2:15])=[CH:10][C:9]=1[NH:17][C:18](=[O:36])[CH2:19][CH:20]([C:26]1[CH:31]=[CH:30][C:29](=[N:2][OH:3])[CH2:28][C:27]=1[O:34][CH3:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH3:5])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 19348778HCID 19348778, compound

Product 1

HCID 86753867HCID 86753867, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

137 mg (1.97 mmol) of hydroxylamine hydrochloride were added to a solution of 398 mg (0.879 mmol) of N-(2-t-butyl-5-carbamoylphenyl)-3-(4-formyl-2-methoxyphenyl)octanamide (prepared as described in Example 110) in 5 ml of pyridine, and the resulting mixture was stirred for 20 minutes. At the end of this time, the reaction mixture was diluted with water, and the diluted aqueous mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. In order to remove the pyridine remaining in the residue, it was dissolved in toluene and the solvent was azeotropically distilled off. Repetition of this procedure gave 414 mg (a quantitative yield) of the title compound as a foam-like substance.

Workup

  1. extractionthe diluted aqueous mixture was extracted with methylene chloride
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed by distillation under reduced pressure
  4. customIn order to remove the pyridine remaining in the residue, it
  5. dissolutionwas dissolved in toluene
  6. distillationthe solvent was azeotropically distilled off

Sources & evidence

ORD record
ord-b569efff215b443d88de51697999ba1c
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

Loading…