Ethylmorpholine → HCID 54377318, compound

HRID 1156476Notes

Reaction equation

HRID 1156476 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)=O.[C:12](#[N:15])[CH:13]=C.C(N1CCOCC1)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(OC)C=CC=CC=1>[CH:7]([C:6]1[CH:10]=[CH:11][C:3]([CH:1]=[CH:13][C:12]#[N:15])=[CH:4][CH:5]=1)=[O:8]

Participants

6

Reactant 3

HCID 7525EthylmorpholineHCID 7855AcrylonitrileHCID 124246204-Formylbenzoyl chloride

Product 1

HCID 54377318HCID 54377318, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7519AnisoleSolvent

Conditions

Temperature
120 °C

Procedure

0.0018 g (0.008 millimol) of palladium acetate, 6.74 g (40 millimols) of 4-formylbenzoyl chloride, 3.29 g (50 millimols) of acrylonitrile and 5.12 ml (40 millimols) of N-ethylmorpholine are added to 80 ml of anisole. The mixture is stirred for 12 hours at 120° C., under argon. The crude product is distilled in vacuo and is then recrystallised from isopropanol. 3.2 g (52% of theory) of 4-formylcinnamonitrile are obtained in the form of white crystals.

Workup

  1. distillationThe crude product is distilled in vacuo
  2. customis then recrystallised from isopropanol

Sources & evidence

ORD record
ord-50fd0df2de054cd5a9f01846ffd56c0f
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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