Hydroxyamine hydrochloride → HCID 178436634, compound

HRID 1908828Notes

Reaction equation

HRID 1908828 reaction equation
Cl.[NH2:2][OH:3].[CH2:4]([C:6]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[C:8]([CH3:14])[N:7]=1)[CH3:5]>CO>[CH2:4]([C:6]1[CH:11]=[C:10]([CH:9]=[C:8]([CH3:14])[N:7]=1)[C:12]([NH:2][OH:3])=[NH:13])[CH3:5]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 670270042-Ethyl-6-methylisonicotinonitrile

Product 1

HCID 178436634HCID 178436634, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled solution of potassium tert.-butylate (7.11 g, 63.4 mmol) in methanol (50 mL), hydroxylamine hydrochloride (3.78 g, 54.4 mmol) is added. The suspension is stirred for 30 min before 2-ethyl-4-cyano-6-methyl-pyridine (2.65 g, 18.1 mmol) is added. The mixture is refluxed for 3 h before it is filtered. The filtrate is evaporated to dryness and the resulting solid is dissolved in water (30 mL) and extracted with EA (3×150 mL). The combined org. extracts are concentrated and dried under HV to give 2-ethyl-N-hydroxy-6-methyl-isonicotinamidine (3.43 g) as a white powder; LC-MS: tR=0.31 min, [M+1]+=180.07; 1H NMR (D6-DMSO) δ 1.22 (t, J=7.5 Hz, 3H), 2.44 (s, 3H), 2.71 (q, J=7.5 Hz, 2H), 5.89 (s, 2H), 7.31 (s, 2H), 9.87 (m, 1H).

Workup

  1. additionis added
  2. additionis added
  3. temperatureThe mixture is refluxed for 3 h before it
  4. filtrationis filtered
  5. customThe filtrate is evaporated to dryness
  6. dissolutionthe resulting solid is dissolved in water (30 mL)
  7. extractionextracted with EA (3×150 mL)
  8. concentrationextracts are concentrated
  9. customdried under HV

Sources & evidence

ORD record
ord-3d74f6b6b9e048ffb8d6b3ac2398e7f0
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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