Hydroxyamine hydrochloride → HCID 178426671, compound

HRID 1908836Notes

Reaction equation

HRID 1908836 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:11])[N:10]=1)[C:6]#[N:7].Cl.[NH2:13][OH:14]>CO>[OH:14][NH:13][C:6](=[NH:7])[C:5]1[CH:8]=[C:9]([CH3:11])[N:10]=[C:3]([CH2:2][OH:1])[CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 178623062-(Hydroxymethyl)-6-methylpyridine-4-carbonitrile

Product 1

HCID 178426671HCID 178426671, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude 2-hydroxymethyl-6-methyl-isonicotinonitrile (544 mg, 2.38 mmol) in methanol (50 mL), potassium tert.-butylate (933 mg, 8.31 mmol) and hydroxylamine hydrochloride (495 mg, 7.13 mmol) is added. The solution is refluxed for 2 h. The resulting suspension is cooled to rt and filtered. The solvent filtrate is evaporated and the remaining residue is suspended in water, filtered off, washed with additional water and dried under HV to give N-hydroxy-2-hydroxymethyl-6-methyl-isonicotinamidine (235 mg) as a beige powder; LC-MS: tR=0.17 min, [M+1]+=182.01; 1H NMR (D6-DMSO): δ 2.45 (s, 3H), 4.52 (d, J=5.8 Hz, 2H), 5.37 (t, J=5.8 Hz, 1H), 5.90 (s, 2H), 7.36 (s, 1H), 7.56 (s, 1H), 9.92 (s, 1H).

Workup

  1. temperatureThe solution is refluxed for 2 h
  2. filtrationfiltered
  3. customThe solvent filtrate is evaporated
  4. filtrationfiltered off
  5. washwashed with additional water
  6. customdried under HV

Sources & evidence

ORD record
ord-d15e0dc7ee0e428ba454f147a151b5d8
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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