Water → 2-Nitrophenylacetonitrile

HRID 1462168Notes

Reaction equation

HRID 1462168 reaction equation
O.[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12](=[N:16]O)C(O)=O)([O-:4])=[O:3]>C(O)(=O)C>[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]#[N:16])([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 962WaterHCID 714366072-(Hydroxyimino)-3-(2-nitrophenyl)propanoic acid

Product 1

HCID 118882-Nitrophenylacetonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Water (50,000 ml), 2,940 ml of glacial acetic acid and (22.22 moles) of 2-nitrophenylpyruvic acid oxime were charged into a 20 gallon reactor. The stirred suspension was heated over two hours under nitrogen atmosphere to 90° and this temperature was maintained for 2 hours. The dark solution was allowed to cool slowly and was stirred overnight at ambient temperature. The suspension was extracted with 5×4,000 ml of methylene chloride, washed with 3×3,000 ml of water, dried over magnesium sulfate and filtered. The filtrate was treated with activated carbon, filtered and the solvent was removed under reduced pressure. The solid residue was recrystallized from 1,000 ml of isopropanol to give 2-nitrophenylacetonitrile, m.p. 82°-84°.

Workup

  1. temperatureThe stirred suspension was heated over two hours under nitrogen atmosphere to 90°
  2. temperaturethis temperature was maintained for 2 hours
  3. temperatureto cool slowly
  4. extractionThe suspension was extracted with 5×4,000 ml of methylene chloride
  5. washwashed with 3×3,000 ml of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. additionThe filtrate was treated with activated carbon
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure
  11. customThe solid residue was recrystallized from 1,000 ml of isopropanol

Sources & evidence

ORD record
ord-9c09d08e3a6843a695830f8b8492816a
Source dataset
uspto-grants-1984_07
Patent number
US04459232

Reaction notes

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