HCID 20362658, compound → HCID 20362654, compound

HRID 1679358Notes

Reaction equation

HRID 1679358 reaction equation
[C:1]([C:3]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:4]=1/[CH:5]=[CH:6]/[C:7](OC)=[O:8])#[N:2]>CO.[Ni]>[CH3:15][C:13]1[CH:12]=[CH:11][C:4]2[CH2:5][CH2:6][C:7](=[O:8])[NH:2][CH2:1][C:3]=2[CH:14]=1

Participants

4

Reactant 1

HCID 20362658HCID 20362658, compound

Product 1

HCID 20362654HCID 20362654, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 27 g. (0.13 moles) of methyl trans-2-cyano-4-methylcinnamate in 1 liter dry methanol is introduced into a 2-liter autoclave. About 5 g. of W-5 Raney nickel are added and the mixture is stirred for 17 hours under a hydrogen pressure (initial pressure 3.5 bars). The reaction mixture is filtered, the catalyst is washed with chloroform and the solvent is removed in vacuo. The red residue obtained is washed with about 20 ml. of 2-propanol and then taken up in hot 2-propanol, whereafter the solution is decolorized over active carbon. After recrystallization, 12.4 g. (53% of theory) of 8-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one are obtained. M.P. 174°-175° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe catalyst is washed with chloroform
  3. customthe solvent is removed in vacuo
  4. customThe red residue obtained
  5. washis washed with about 20 ml
  6. customAfter recrystallization, 12.4 g

Sources & evidence

ORD record
ord-4211579c1ad44ddfa01a58733191ee37
Source dataset
uspto-grants-1978_03
Patent number
US04080449

Reaction notes

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