Acrylonitrile → HCID 70631280, compound

HRID 259116Notes

Reaction equation

HRID 259116 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH3:5][O:6][CH:7]1[C:16]2[CH2:15][CH2:14][CH2:13][CH:12]3[CH2:17][CH2:18][O:19][C:10]([C:11]=23)=[CH:9][N:8]1[O:20][CH3:21].[OH-].[Na+]>O1CCOCC1>[C:1]([CH2:2][CH2:3][CH:14]1[CH2:15][C:16]2[CH:7]([O:6][CH3:5])[N:8]([O:20][CH3:21])[CH:9]=[C:10]3[O:19][CH2:18][CH2:17][CH:12]([C:11]=23)[CH2:13]1)#[N:4]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 20523931HCID 20523931, compound

Product 1

HCID 70631280HCID 70631280, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of acrylonitrile (12 ml) and 1,2,3a,4,5,6-hexahydro-7,8-dimethoxypyrano[2,3,4-de]isoquinoline (11 g), described in Example 56, in dioxane (80 ml) and 10% NaOH solution (2.5 ml) is heated and stirred on the steam bath for 24 hr. The mixture is evaporated and the residue is dissolved in a mixture of ether and a little chloroform. The solution is extracted with 2N HCl and the extracts are washed (brine), dried and evaporated. The residue is crystallized from ether and then from benzene-hexane to give the title compound, m.p. 105°-107° C.

Workup

  1. customThe mixture is evaporated
  2. dissolutionthe residue is dissolved in a mixture of ether
  3. extractionThe solution is extracted with 2N HCl
  4. washthe extracts are washed (brine)
  5. customdried
  6. customevaporated
  7. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-93bb737e32da4709a20e36224059ef9a
Source dataset
uspto-grants-1977_07
Patent number
US04036842

Reaction notes

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