p-Nitroacetophenone → (2E)-3-(dimethylamino)-1-(4-nitrophenyl)prop-2-en-1-one

HRID 2361489Notes

Reaction equation

HRID 2361489 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>>[CH3:15][N:16]([CH3:18])/[CH:17]=[CH:11]/[C:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)=[O:12]

Participants

3

Reactant 2

HCID 7487p-NitroacetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 1475992(2E)-3-(dimethylamino)-1-(4-nitrophenyl)prop-2-en-1-one

Procedure

A solution of 1-(4-nitrophenyl)ethanone (2.2 g, 13 mmol) and N,N-dimethylformamide dimethyl acetal (25 ml) was heated to 120° C. in a sealed tube overnight. The volatiles were removed. The residue was dissolved in DCM and washed twice with H2O. The DCM layer was dried with MgSO4. The crude product was purified by flash chromatography (silica gel, 100% EtOAc) to isolate (E)-3-(dimethylamino)-1-(4-nitrophenyl)prop-2-en-1-one (2.2 g,) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 2.99 (s, 3H), 3.23 (s, 3H), 5.70 (d, J=12.4 Hz, 1H), 7.94 (d, J=12.4 Hz, 1H), 8.03 (m, 2H), 8.26 (m, 2H). MS (ESI): 221 (M+H+)

Workup

  1. customThe volatiles were removed
  2. dissolutionThe residue was dissolved in DCM
  3. washwashed twice with H2O
  4. dry with materialThe DCM layer was dried with MgSO4
  5. customThe crude product was purified by flash chromatography (silica gel, 100% EtOAc)

Sources & evidence

ORD record
ord-af6572cc5dea4fd7aba517af90d7dac7
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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