Dimethylformamide → Ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate

HRID 526438Notes

Reaction equation

HRID 526438 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)#[N:2].[CH3:15][N:16]([CH:18]=O)[CH3:17]>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[CH:15][N:16]([CH3:18])[CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 279718Ethyl 2-(4-cyanophenyl)acetate

Product 1

HCID 117601544Ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylateYield 62%

Procedure

Combined ethyl 2-(4-cyanophenyl)acetate (25 g, 0.132 mol) with DMF-DEA (60 mL) and heated to 70° C. for 3 hours. The reaction mixture was cooled to room temperature and concentrated and then purified by flash chromatography to give the title compound (20 g, 62%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.71 (d, J=8.4 Hz, 2H), 7.59 (s, 1H), 7.29 (d, J=8.4 Hz, 2H), 4.03 (q, J=6.8 Hz, 2H), 2.67 (s, 6H), 1.13 (t, J=6.8 Hz, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-989e8d0b337c4bf5b31c150acb0ff36a
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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