Hydroxyamine hydrochloride → HCID 136413234, compound

HRID 572688Notes

Reaction equation

HRID 572688 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.Cl.[NH2:13][OH:14]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[N:13][OH:14])[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86675935HCID 86675935, compound

Product 1

HCID 136413234HCID 136413234, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-chloro-2-methyl-3-oxo-2,3-dihydropyridazine-4-carbaldehyde (2 g, 11.59 mmol, Preparation #30) in MeOH (30 mL) was added a solution of hydroxylamine hydrochloride (0.966 g, 13.91 mmol) in water (5 mL) and heated to about 70° C. for 1 h. The mixture was cooled to RT and solids obtained were collected by filtration to afford the 6-chloro-2-methyl-3-oxo-2,3-dihydropyridazine-4-carbaldehyde oxime 1.6 g, (73.6%) as an off white solid. 1H NMR (400 MHz, DMSO) δ 12.316 (s, 1H), 8.092 (s, 1H), 7.675 (s, 1H), 3.651 (s, 3H); MS m/z: 185.7 (M−H)−

Workup

  1. temperatureThe mixture was cooled to RT
  2. customsolids obtained
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-a960137441944cc1aa51ef528d431c27
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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