Hydroxyamine hydrochloride → HCID 136331521, compound

HRID 1961718Notes

Reaction equation

HRID 1961718 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([CH:22]=O)=[N:11][CH:12]=[C:13]([N:15]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[N:16]3)[N:14]=2)=[CH:4][CH:3]=1.Cl.[NH2:25][OH:26]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([CH:22]=[N:25][OH:26])=[N:11][CH:12]=[C:13]([N:15]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[N:16]3)[N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 59570680HCID 59570680, compound

Product 1

HCID 136331521HCID 136331521, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-Chloro-phenylamino)-5-(3,5-dimethyl-pyrazol-1-yl) -pyrazine-2-carbaldehyde (100 mg, 0.27 mmol) was dissolved in ethanol (99%, 10 mL) and hydroxylamine, hydrochloride (20 mg, 0.27 mmol) was added. The mixture was heated to reflux for 3 hours and concentrated in vacuo. Ethyl acetate (30 mL) and aqeuous sodium carbonate (20 mL) were added and stirred for 15 minutes. The layers were separated and the organic phase was washed with brine, dried over sodium sulphate, filtrated and concentrated in vacuo to give 3-(4-chloro-phenylamino)-5-(3,5-dimethyl-pyrazol-1-yl)-pyrazine-2-carbaldehyde oxime (71 mg, 76%) as an orange solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. additionEthyl acetate (30 mL) and aqeuous sodium carbonate (20 mL) were added
  5. customThe layers were separated
  6. washthe organic phase was washed with brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltrated
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8840095af78e4688bea757e2041a79db
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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