Hydroxyamine hydrochloride → HCID 178499428, compound

HRID 2172680Notes

Reaction equation

HRID 2172680 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1.Cl.[NH2:15][OH:16].C(=O)(O)[O-].[Na+]>CO.CCOC(C)=O.O>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[NH:12])[NH:15][OH:16])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 1512619Methyl (4-cyanophenyl)acetate

Product 1

HCID 178499428HCID 178499428, compoundYield 95.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

(4-Cyano-phenyl)-acetic acid methylester (1.054 g, 6.02 mmol), hydroxylamine hydrochloride (0.690 g, 9.93 mmol) and sodium bicarbonate (0.834 g, 9.93 mmol) were dissolved in MeOH (12.03 mL) at RT. The mixture was stirred at 60° C. for 5 h, diluted with EtOAc (200 mL) and 40 ml water added. The aqueous layer was extracted with EtOAc (100 mL). The combined organic phases were washed with brine (40 mL) and dried over sodium sulfate. Solvent was removed to yield 1.2 g (5.76 mmol) of yellow oil, which was dried on high vacuum over night. The crude mixture was used without further purification.

Workup

  1. additionadded
  2. extractionThe aqueous layer was extracted with EtOAc (100 mL)
  3. washThe combined organic phases were washed with brine (40 mL)
  4. dry with materialdried over sodium sulfate
  5. customSolvent was removed

Sources & evidence

ORD record
ord-9641b71ae1ea43e8957537e25196c82f
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

Loading…