Methanol → HCID 178510828, compound

HRID 1509053Notes

Reaction equation

HRID 1509053 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][OH:14].Cl.C([O-])(O)=O.[Na+].CO>O>[OH:14][NH:13][C:11](=[NH:12])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 68386p-NitrophenylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178510828HCID 178510828, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250-mL round bottomed flask was charged with 2-(4-nitrophenyl)acetonitrile (2.5 g, 15.4 mmol, 1 eq.), NH2OH/HCl (2.12 g, 31 mmol, 2 eq), NaHCO3 (2.82 g, 2.3 mol, 7 eq.), MeOH (100 ml) and water (16 ml). The mixture was stirred under reflux overnight. After cooling to room temperature, the volatile material was removed under reduced pressure. The residue was treated with water (100 ml). Solid was collected by filtration and washed with water (3×20 ml) followed by dichloromethane (3×10 ml). After drying, the title compound was obtained as yellowish solid (2.46 g, 84% yield).

Workup

  1. temperatureunder reflux overnight
  2. customthe volatile material was removed under reduced pressure
  3. additionThe residue was treated with water (100 ml)
  4. filtrationSolid was collected by filtration
  5. washwashed with water (3×20 ml)
  6. customAfter drying

Sources & evidence

ORD record
ord-508e870161f34d128a38c048aa7a27e9
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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