Dimethylformamide dimethyl acetal → 1-(3-Cyanophenyl)-3-(dimethylamino)acrolein

HRID 44958

Reaction equation

HRID 44958 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])(=[O:3])[CH3:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[CH3:14][N:15]([CH3:17])/[CH:16]=[CH:2]/[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 802223-Acetylbenzonitrile

Product 1

HCID 57140731-(3-Cyanophenyl)-3-(dimethylamino)acrolein

Conditions

Temperature
120 °C

Procedure

3-Acetylbenzonitrile (0.435 g, 0.00300 mol) and 1,1-dimethoxy-N,N-dimethylmethanamine (0.400 mL, 0.00301 mol) were combined and heated in sealed tube to 120° C. in the microwave for 15 min. The reaction was then allowed to cool to rt giving the 3-[(2E)-3-(dimethylamino)prop-2-enoyl]-benzonitrile as a red-orange crystalline material, LC/MS (M+H)+: 201.

Workup

  1. temperatureto cool to rt

Sources & evidence

ORD record
ord-ba107af0ecdd4e85bcb58a3b397df2c1
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Linked notes

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