Water → 2-Nitrophenylacetonitrile

HRID 1462435Notes

Reaction equation

HRID 1462435 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 are charged into a 20 gallon reactor. The stirred suspension is heated over two hours under nitrogen atmosphere to 90° and this temperature is maintained for 2 hours. The dark solution is allowed to cool slowly and is stirred overnight at ambient temperature. The suspension is 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 is treated with activated carbon, filtered and the solvent is removed under reduced pressure. The solid residue is recrystallized from 1,000 ml of isopropanol to give 2-nitrophenylacetonitrile, m.p. 82°-84°.

Workup

  1. temperatureThe stirred suspension is heated over two hours under nitrogen atmosphere to 90°
  2. temperaturethis temperature is maintained for 2 hours
  3. temperatureto cool slowly
  4. extractionThe suspension is 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 is treated with activated carbon
  9. filtrationfiltered
  10. customthe solvent is removed under reduced pressure
  11. customThe solid residue is recrystallized from 1,000 ml of isopropanol

Sources & evidence

ORD record
ord-88d6a1cd727b4c9db552da382025dcb9
Source dataset
uspto-grants-1984_07
Patent number
US04460587

Reaction notes

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