Hydroxyamine hydrochloride → 5-Bromo-2-propoxybenzonitrile

HRID 1978683Notes

Reaction equation

HRID 1978683 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][CH3:13])=[C:6]([CH:9]=1)[CH:7]=O.Cl.[NH2:15]O>C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][CH3:13])=[C:6]([CH:9]=1)[C:7]#[N:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 20640255-bromo-2-propoxybenzaldehyde

Product 1

HCID 196177395-Bromo-2-propoxybenzonitrileYield 73.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

In formic acid (110 ml) was dissolved 5-bromo-2-propoxybenzaldehyde (21.8 g). To the mixture was added hydroxylamine hydrochloride (9.4 g), and the mixture was refluxed for 7 hours and cooled to room temperature. Under reduced pressure, the solvent was evaporated, and the residue was added to 1N potassium hydroxide. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1) to give 5-bromo-2-propoxybenzonitrile (15.8 g).

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionthe residue was added to 1N potassium hydroxide
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated
  8. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-334119bf56ff4d7c844b4b5c0cb3fffc
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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