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

HRID 1258195Notes

Reaction equation

HRID 1258195 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-95c58dcc83f34341b29b382556342f58
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

Loading…