Hydroxylamine HCl → 2-Chloro-3-hydroxybenzonitrile

HRID 225821Notes

Reaction equation

HRID 225821 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[Cl-].O[NH3+:13]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:13]

Participants

5

Reactant 2

HCID 21645Hydroxylamine HClHCID 5933762-Chloro-3-hydroxybenzaldehyde

Product 1

HCID 214365452-Chloro-3-hydroxybenzonitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-3-hydroxybenzaldehyde [(2 g, 12.8 mmol) WO 2005007633, p34] and hydroxyl ammonium chloride (1.33 g, 19.6 mmol) in acetic acid (20 mL) was heated under reflux for 2 hours. The reaction mixture was then cooled to room temperature and partitioned between diethyl ether and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated in vacuo to give a white solid. The solid was then dissolved in ethyl acetate washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a solid in quantitative yield.

Workup

  1. temperatureunder reflux for 2 hours
  2. custompartitioned between diethyl ether and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a white solid
  8. washwashed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ada5673d3bfe4b2b954acd2604a1bd63
Source dataset
uspto-grants-2009_07
Patent number
US07557131B2

Reaction notes

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