Hydrochloric Acid → HCID 20362668, compound

HRID 1679364Notes

Reaction equation

HRID 1679364 reaction equation
[CH3:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][C:4](=[O:13])[CH2:3]1.[OH-].[CH2:15]([N+:22](C)(C)C)[C:16]1C=CC=C[CH:17]=1.C(#N)C=C.Cl>O.N1C=CC=CC=1>[C:15]([CH2:16][CH2:17][N:5]1[C:4](=[O:13])[CH2:3][CH:2]([CH3:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6]1)#[N:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 20362671HCID 20362671, compound

Product 1

HCID 20362668HCID 20362668, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of 6 g. (0.034 moles) of 5-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one and 4 drops of Triton B (benzyltrimethylammonium hydroxide) in 10 ml. of pyridine, are added dropwise 2 g. (0.038 moles) of acrylonitrile dissolved in 2.5 ml. of pyridine. The reaction mixture is heated to 80° C. for 2 hours and then poured into iced water. It is acidified with hydrochloric acid to pH 4 and extracted with chloroform. The organic phase is washed neutral with water and then dried over anhydrous sodium sulfate. It is filtered and the solvent is evaporated off in vacuo. 8 g. (almost theoretical yield) of syrupy 2-(2-cyanoethyl)-5-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one are obtained.

Workup

  1. additionTo a mixture of 6 g
  2. extractionextracted with chloroform
  3. washThe organic phase is washed neutral with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationIt is filtered
  6. customthe solvent is evaporated off in vacuo

Sources & evidence

ORD record
ord-8632456fe32c4505a8bd0620f84bf4ad
Source dataset
uspto-grants-1978_03
Patent number
US04080449

Reaction notes

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