Hydrochloric Acid → 3-(3,4-Dimethoxyphenyl)propanenitrile

HRID 1624862Notes

Reaction equation

HRID 1624862 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[BH4-].[Na+].Cl>N1C=CC=CC=1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 15509583-(3,4-Dimethoxyphenyl)acrylonitrileHCID 4311764Sodium borohydride

Product 1

HCID 3199323-(3,4-Dimethoxyphenyl)propanenitrileYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

To a solution of 1 g (5.3 mmoles) of (2E)-3-(3,4-dimethoxyphenyl)prop-2-enenitrile in 9.3 mL of pyridine and 2.8 mL of methanol there is added, little by little, 0.24 g of NaBH4 (6.3 mmol, 1.2 eq.). The reaction mixture is heated at reflux for 9 hours. After cooling to ambient temperature, the reaction mixture is added to a solution of 9 mL of hydrochloric acid 37% in 24 g of ice. The solution is extracted twice with dichloromethane. The organic phases are collected and the solvent is evaporated off under reduced pressure to yield 0.82 g of a red-brown oil which crystallises.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 9 hours
  3. extractionThe solution is extracted twice with dichloromethane
  4. customThe organic phases are collected
  5. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-6fd9ba728c8f42938663b91a21c24f95
Source dataset
uspto-grants-2014_07
Patent number
US08779122B2

Reaction notes

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