Hydrochloric Acid → (4-Methoxy-5-methyl-2-nitrophenyl)acetonitrile

HRID 881608Notes

Reaction equation

HRID 881608 reaction equation
COC(=O)[CH:4]([C:17]#[N:18])[C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15].Cl>CO>[CH3:13][O:12][C:8]1[C:9]([CH3:11])=[CH:10][C:5]([CH2:4][C:17]#[N:18])=[C:6]([N+:14]([O-:16])=[O:15])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58437260Cyano-(4-methoxy-5-methyl-2-nitrophenyl)acetic acid methyl ester

Product 1

HCID 58437287(4-Methoxy-5-methyl-2-nitrophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cyano-(4-methoxy-5-methyl-2-nitrophenyl)acetic acid methyl ester in methanol (1.7 mL) was added 6 mol/L hydrochloric acid (1.7 mL), and this mixture was heated under reflux for 9 hours. After cooling to ambient temperature, this organic solvent was removed under reduced pressure and resulting mixture was extracted with ethyl acetate. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.25 g).

Workup

  1. temperaturethis mixture was heated
  2. temperatureunder reflux for 9 hours
  3. customthis organic solvent was removed under reduced pressure
  4. customresulting mixture
  5. extractionwas extracted with ethyl acetate
  6. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6e51642908fe4dfe8510eef706bd0598
Source dataset
uspto-grants-2015_03
Patent number
US08993616B2

Reaction notes

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