Water → HCID 178513281, compound

HRID 1993802Notes

Reaction equation

HRID 1993802 reaction equation
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:10][OH:11].C([O-])([O-])=O.[K+].[K+].O>C(O)C>[OH:11][NH:10][C:1](=[NH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7505BenzonitrileHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513281HCID 178513281, compoundYield 305.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Benzonitrile (1 ml, 9.79 mmol) was mixed with hydroxylamine hydrochloride (1.36 g, 1.96 mmol) and K2CO3 (2.71 g, 1.96 mmol) in anhydrous ethanol (15 ml). The solution was stirred at 80° C. for 16 hr. Water was added and the aqueous phase was extracted with EtOAc (3×), dried over MgSO4 and the volatiles removed in vacuo to give a viscous oil (816 mg, 5.99 mmol, 62%). The compound 10A was used for next step without any further purification. HPLC (4 minutes gradient) tR 0.62 min; MS m/z 137.06 [M+H]+.

Workup

  1. extractionthe aqueous phase was extracted with EtOAc (3×)
  2. dry with materialdried over MgSO4
  3. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-bc54ad3f9595438f932dd215a1327a95
Source dataset
uspto-grants-2010_01
Patent number
US07652044B2

Reaction notes

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