Ammonia → 3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile

HRID 1624858Notes

Reaction equation

HRID 1624858 reaction equation
N.Br[C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([O:11][CH3:12])=[CH:5][C:4]=1[CH2:13][CH2:14][C:15]#[N:16]>>[CH3:12][O:11][C:6]1[CH:5]=[C:4]2[C:3](=[CH:8][C:7]=1[O:9][CH3:10])[CH:14]([C:15]#[N:16])[CH2:13]2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 3204113-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile

Product 1

HCID 2905443,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrileYield 74%

Procedure

To a solution of NaNH2, prepared starting from 200 mL of liquid NH3 and 1 g of Na (catalyst: FeCl3) there are added, in portions, 5.4 g of 3-(2-bromo-4,5-dimethoxyphenyl)propanenitrile and the reaction mixture is stirred at ambient temperature for 2 hours. After evaporating off the excess NH3, 2 g of NH4Cl and 200 mL of water are added in portions. The grey crystals formed are collected and recrystallised from ethanol to yield 2.38 g of the expected product.

Workup

  1. customAfter evaporating off the excess NH3, 2 g of NH4Cl and 200 mL of water
  2. additionare added in portions
  3. customThe grey crystals formed
  4. customare collected
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-4424660f48124784b4e77e5a02ad28d4
Source dataset
uspto-grants-2014_07
Patent number
US08779121B2

Reaction notes

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