Hydroxyamine hydrochloride → HCID 178426674, compound

HRID 1908833Notes

Reaction equation

HRID 1908833 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][N:5]([CH3:15])[C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH3:14])[N:13]=1)[C:9]#[N:10]>CO>[CH3:4][N:5]([CH3:15])[C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([CH3:14])[N:13]=1)[C:9]([NH:2][OH:3])=[NH:10]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 669334682-Dimethylamino-6-methylisonicotinonitrile

Product 1

HCID 178426674HCID 178426674, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled solution of potassium tert.-butylate (1.71 g, 15.2 mmol) in methanol (50 mL), hydroxylamine hydrochloride (905 mg, 13.02 mmol) is added. The suspension is stirred for 30 min before 2-dimethylamino-6-methyl-isonicotinonitrile (699 mg, 4.34 mmol) is added. The mixture is refluxed for 2 h before it is evaporated. The residue is dissolved in a small amount of water and separated by MPLC on RP-C18-silica gel to give 2-dimethylamino-N-hydroxy-6-methyl-isonicotinamidine (284 mg) as a brownish resin; LC-MS: tR=0.60 min, [M+1]+=195.42.

Workup

  1. additionis added
  2. additionis added
  3. temperatureThe mixture is refluxed for 2 h before it
  4. customis evaporated
  5. dissolutionThe residue is dissolved in a small amount of water
  6. customseparated by MPLC on RP-C18-silica gel

Sources & evidence

ORD record
ord-e9da8ceb1cf44d81a8a28a652e2f5a74
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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