Hydroxyamine hydrochloride → HCID 178426675, compound

HRID 2065895Notes

Reaction equation

HRID 2065895 reaction equation
CC([O-])(C)C.[K+].Cl.[NH2:8][OH:9].[CH2:10]([C:14]1[C:21]([CH3:22])=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1)[CH:11]([CH3:13])[CH3:12]>CO>[OH:9][NH:8][C:18](=[NH:19])[C:17]1[CH:20]=[C:21]([CH3:22])[C:14]([CH2:10][CH:11]([CH3:12])[CH3:13])=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23665647Potassium tert-butoxideHCID 670269756-Isobutyl-5-methylnicotinonitrile

Product 1

HCID 178426675HCID 178426675, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of potassium tert-butylate (3.04 g, 27.1 mmol) in MeOH (60 mL), hydroxylamine hydrochloride (1.62 g, 23.2 mmol) is added at 0° C. To this suspension, 6-isobutyl-5-methyl-nicotinonitrile (1.35 g, 7.75 mmol) is added. The mixture is refluxed for 3 h, cooled to rt, filtered and the filtrate is evaporated to dryness. The residue is suspended in a small amount of water and then extracted with EA. The org. extract is concentrated and dried under high vacuum to give N-hydroxy-6-isobutyl-5-methyl-nicotinamidine (1.53 g) as a pale yellow oil; LC-MS: tR=0.68 min, [M+1]+=208.22; 1H NMR (D6-DMSO): δ 0.91 (d, J=6.8 Hz, 6H), 2.06-2.17 (m, 1H), 2.29 (s, 3H), 2.61 (d, J=7.0 Hz, 2H), 5.85 (s br, 2H), 7.76 (s, 1H), 8.60 (s, 1H), 9.68 (s, 1H).

Workup

  1. temperatureThe mixture is refluxed for 3 h
  2. filtrationfiltered
  3. customthe filtrate is evaporated to dryness
  4. extractionextracted with EA
  5. extractionextract
  6. concentrationis concentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-c85e72adabb6498d910493f5026733bc
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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