Hydroxyamine hydrochloride → HCID 178436634, compound

HRID 1924829Notes

Reaction equation

HRID 1924829 reaction equation
CC([O-])(C)C.[K+].Cl.[NH2:8][OH:9].[CH2:10]([C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([CH3:20])[N:19]=1)[C:15]#[N:16])[CH3:11]>CO>[CH2:10]([C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([CH3:20])[N:19]=1)[C:15]([NH:8][OH:9])=[NH:16])[CH3:11]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 670270042-Ethyl-6-methylisonicotinonitrile

Product 1

HCID 178436634HCID 178436634, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., KOtBu (1.81 g, 16.2 mmol) is carefully added to methanol (25 mL). Hydroxylamine hydrochloride (963 mg, 13.9 mmol) is then added to this solution. The suspension is stirred for 30 min before 2-ethyl-6-methyl-isonicotinonitrile (675 mg, 4.62 mmol) is added. The mixture is refluxed for 1 h, the solvent is evaporated. The residue is dissolved in water, extracted three times with EA. The org. extracts are dried over MgSO4, filtered, evaporated and dried under HV to give 2-ethyl-N-hydroxy-6-methyl-isonicotinamidine (897 mg) as a white powder, LC-MS: tR=0.31 min, [M+1]+=180.32.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for 1 h
  3. customthe solvent is evaporated
  4. dissolutionThe residue is dissolved in water
  5. extractionextracted three times with EA
  6. dry with materialextracts are dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customdried under HV

Sources & evidence

ORD record
ord-247efcd1836245d7910b02d86dcdb6ee
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

Loading…