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

HRID 1624856Notes

Reaction equation

HRID 1624856 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

Conditions

Temperature
100 °C

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 (100° C.) 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. temperatureAfter cooling to ambient temperature
  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-2b7a03b3307443438c5fe868adeec14b
Source dataset
uspto-grants-2014_07
Patent number
US08779121B2

Reaction notes

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