Potassium Carbonate → HCID 178485436, compound

HRID 2172678Notes

Reaction equation

HRID 2172678 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:20][OH:21]>CCO.CCOC(C)=O>[OH:21][NH:20][C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=[NH:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 50807374-Cyano-N-methylbenzamide

Product 1

HCID 178485436HCID 178485436, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-Cyano-N-methylbenzamide (200 mg, 1.249 mmol), potassium carbonate (1035 mg, 7.49 mmol) and hydroxylamine hydrochloride (521 mg, 7.49 mmol) were dissolved in EtOH (12.6 mL). The reaction mixture was stirred at 80° C. for 25 h. The reaction mixture was diluted with EtOAc (50 mL), washed with water (10 mL), water phase extracted with EtOAc (20 mL). Combined organic phases were washed with brine (10 mL) and dried over sodium sulfate. The solvent was removed to yield 227 mg of a white powdery solid. The crude material was used without further purification.

Workup

  1. washwashed with water (10 mL), water phase
  2. extractionextracted with EtOAc (20 mL)
  3. washCombined organic phases were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-e071ebb4d1784ee998a92ace72622359
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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