2-(4-Chlorophenoxy)acetonitrile → 79295-18-4

HRID 1667288Notes

Reaction equation

HRID 1667288 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][CH:3]=1.Cl.[NH2:13][OH:14].C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7]/[C:8](=[N:13]/[OH:14])/[NH2:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 958065979295-18-4

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(4-chlorophenoxy)acetonitrile (1.35 g, 8.06 mmol), hydroxylamine hydrochloride (0.840 g, 12.1 mmol), and sodium hydrogencarbonate (3.38 g, 40.3 mmol) in methanol (15 mL) was heated to reflux. After 16 hours, the reaction mixture was cooled to ambient temperature and filtered. The filtrate was diluted with ethyl acetate (125 mL) and washed with 1 N aqueous HCl and saturated aqueous NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo to furnish the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.28 (s, 1H), 7.36-7.28 (m, 2H), 7.06-6.98 (m, 2H), 5.60 (bs, 2H), 4.39 (s, 2H); MS (DCI+) m/z 201 (M+H)+.

Workup

  1. temperaturewas heated to reflux
  2. filtrationfiltered
  3. additionThe filtrate was diluted with ethyl acetate (125 mL)
  4. washwashed with 1 N aqueous HCl and saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e598d9d1257441468476c497498bffe4
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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