Sodium Carbonate → 2-(4-Methoxy-2-nitrophenyl)acetonitrile

HRID 1913427Notes

Reaction equation

HRID 1913427 reaction equation
C(OC(=O)[CH:5]([C:17]#[N:18])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[N+:14]([O-:16])=[O:15])C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:17]#[N:18])=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 11086625Cyano-(4-methoxy-2-nitro-phenyl)-acetic acid ethyl ester

Product 1

HCID 111831262-(4-Methoxy-2-nitrophenyl)acetonitrileYield 37.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To cyano-(4-methoxy-2-nitro-phenyl)-acetic acid ethyl ester (945 mg, 3.58 mmol) was added 30 mL of a saturated solution of aqueous sodium carbonate. The mixture was stirred overnight at 55° C. After cooling to room temperature, the mixture was diluted with ethyl acetate. The organic layer was washed with saturated brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified on a Biotage (Biotage Inc.) 10 g silica column, eluting with 0-40% EtOAc in heptanes to provide 258 mg (37%) of (4-methoxy-2-nitro-phenyl)-acetonitrile.

Workup

  1. temperatureAfter cooling to room temperature
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified on a Biotage (Biotage Inc.) 10 g silica column
  6. washeluting with 0-40% EtOAc in heptanes

Sources & evidence

ORD record
ord-476090a1aeef4579b2202e504531375b
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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