Hydroxyamine hydrochloride → HCID 178499428, compound

HRID 2065902Notes

Reaction equation

HRID 2065902 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:15][OH:16].C([O-])(O)=O.[Na+]>CO>[OH:16][NH:15][C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1)=[NH:2]

Participants

5

Reactant 3

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

Product 1

HCID 178499428HCID 178499428, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl (4-cyanophenyl)acetate (4.00 g, 27.8 mmol) in MeOH (20 mL), hydroxylamine hydrochloride (3.17 g, 45.7 mmol) and NaHCO3 (3.84 g, 45.7 mmol) is added. The suspension is stirred at 60° C. for 18 h before it is filtered and the filtrate is concentrated. The residue is dissolved in DCM, washed with water followed by brine, dried over MgSO4, filtered, concentrated and dried to give methyl [4-(N-hydroxycarbamimidoyl)-phenyl]-acetate (3.67 g) as a colourless oil; LC-MS: tR=0.50 min, [M+1]+=209.05.

Workup

  1. filtrationis filtered
  2. concentrationthe filtrate is concentrated
  3. dissolutionThe residue is dissolved in DCM
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried

Sources & evidence

ORD record
ord-e96e798c0ec14401a8723b5715641013
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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