Hydroxyamine hydrochloride → HCID 178426670, compound

HRID 1908825Notes

Reaction equation

HRID 1908825 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][C:5]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]([CH3:13])[N:6]=1>CO>[OH:3][NH:2][C:11](=[NH:12])[C:9]1[CH:8]=[C:7]([CH3:13])[N:6]=[C:5]([CH3:4])[CH:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 123685422,6-Dimethylpyridine-4-carbonitrile

Product 1

HCID 178426670HCID 178426670, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To an ice-cooled solution of potassium tert.-butylate (1.25 g, 11.1 mmol) in methanol (20 mL), hydroxylamine hydrochloride (773 mg, 11.1 mmol) is added. The suspension is stirred for 30 min before 2,6-dimethyl-4-cyano-pyridine (490 mg, 3.71 mmol) is added. The mixture is stirred at 60° C. for 15 h before it is filtered. The filtrate is evaporated to dryness and the resulting solid is washed with water and then dried under HV to give N-hydroxy-2,6-dimethyl-isonicotinamidine (503 mg) as a white powder; LC-MS: tR=0.23 min; [M+1]+=166.01; 1H NMR (D6-DMSO): δ 2.43 (s, 6H), 5.88 (s, 2H), 7.30 (s, 2H), 9.90 (s, 1H).

Workup

  1. additionis added
  2. additionis added
  3. filtrationis filtered
  4. customThe filtrate is evaporated to dryness
  5. washthe resulting solid is washed with water
  6. customdried under HV

Sources & evidence

ORD record
ord-a4ae3040656c44a88009ce4892e65cfd
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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