Hydroxyamine hydrochloride → HCID 178463822, compound

HRID 1908847Notes

Reaction equation

HRID 1908847 reaction equation
Cl.[NH2:2][OH:3].[CH2:4]([N:6]([CH2:16][CH3:17])[C:7]1[N:12]=[C:11]([C:13]#[N:14])[CH:10]=[C:9]([CH3:15])[CH:8]=1)[CH3:5]>CO>[CH2:16]([N:6]([CH2:4][CH3:5])[C:7]1[N:12]=[C:11]([C:13]([NH:2][OH:3])=[NH:14])[CH:10]=[C:9]([CH3:15])[CH:8]=1)[CH3:17]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 67026915HCID 67026915, compound

Product 1

HCID 178463822HCID 178463822, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (0° C.) solution of potassium tert.-butylate (494 mg, 4.40 mmol) in methanol (10 mL), hydroxylamine hydrochloride (262 mg, 3.73 mmol) is added. The mixture is stirred for 30 min before 6-diethylamino-4-methyl-pyridine-2-carbonitrile (238 mg, 1.26 mmol) is added. Stirring is continued at rt for 18 h before the solvent is evaporated. The residue is dissolved in 1 N aq. HCl. The solution is extracted with EA. The pH of the aq. phase is adjusted to pH ˜9 by adding sat. aq. NaHCO3. The mixture is extracted with EA and the org. extract is dried over MgSO4, filtered, concentrated and dried to give 6-diethylamino-N-hydroxy-4-methyl-pyridine-2-carboxamidine (241 mg) as a yellow oil; LC-MS: tR=0.69 min, [M+1]+=223.05.

Workup

  1. additionis added
  2. customis evaporated
  3. dissolutionThe residue is dissolved in 1 N aq. HCl
  4. extractionThe solution is extracted with EA
  5. additionby adding sat. aq. NaHCO3
  6. extractionThe mixture is extracted with EA
  7. extractionextract
  8. dry with materialis dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried

Sources & evidence

ORD record
ord-e564830338a8463d8a53d15740aff81e
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

Loading…