Hydroxyamine hydrochloride → HCID 178426675, compound

HRID 1908838Notes

Reaction equation

HRID 1908838 reaction equation
Cl.[NH2:2][OH:3].[CH2:4]([C:8]1[C:15]([CH3:16])=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=1)[CH:5]([CH3:7])[CH3:6]>CO>[OH:3][NH:2][C:12](=[NH:13])[C:11]1[CH:14]=[C:15]([CH3:16])[C:8]([CH2:4][CH:5]([CH3:6])[CH3:7])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 670269756-Isobutyl-5-methylnicotinonitrile

Product 1

HCID 178426675HCID 178426675, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled solution of potassium tert.-butylate (284 g, 2.53 mmol) in methanol (4 mL), hydroxylamine hydrochloride (151 mg, 2.17 mmol) is added. The suspension is stirred for 30 min before 6-isobutyl-5-methyl-nicotinonitrile (126 mg, 0.723 mmol) is added. The mixture is refluxed for 1 h before the solvent is evaporated. The residue is dissolved in sat. aq. NaHCO3-solution (10 mL) and extracted with EA (3×15 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried under HV to give N-hydroxy-6-isobutyl-5-methyl-nicotinamidine (143 mg) as a white solid; LC-MS: tR=0.56 min, [M+1]+=208.13; 1H NMR (CDCl3): δ 0.97 (d, J=6.8 Hz, 6H), 2.16 (hept, J=7.0 Hz, 1H), 2.36 (s, 3H), 2.72 (d, J=7.3 Hz, 2H), 4.91 (s, 2H), 7.70 (d, J=1.3 Hz, 1H), 8.66 (d, J=1.8 Hz, 1H).

Workup

  1. additionis added
  2. additionis added
  3. temperatureThe mixture is refluxed for 1 h before the solvent
  4. customis evaporated
  5. dissolutionThe residue is dissolved in sat. aq. NaHCO3-solution (10 mL)
  6. extractionextracted with EA (3×15 mL)
  7. dry with materialextracts are dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried under HV

Sources & evidence

ORD record
ord-b9cc711c547b47ceb9b714152e0c048f
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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