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

HRID 2361494Notes

Reaction equation

HRID 2361494 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=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:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:12]

Participants

3

Reactant 2

HCID 8494m-NitroacetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5375681(2E)-3-(dimethylamino)-1-(3-nitrophenyl)prop-2-en-1-one

Conditions

Temperature
115 °C

Procedure

To a sealed tube equipped with a magnetic stir bar, containing 1,1-dimethoxy-N,N-dimethylmethanamine (50 mL) was placed 1-(3-nitrophenyl)ethanone (5 g, 30 mmol, 1.0 equiv). The reaction was allowed to stir at 115° C. for 15 h. After the reaction was complete by LCMS, the solid product was filtered and washed with ether to yield 5.3 g (80%) of DHK-7-12 as an yellow solid. MS (ESI, Pos.) m/z: 221.1 [M+H]+.

Workup

  1. customTo a sealed tube equipped with a magnetic stir bar
  2. filtrationthe solid product was filtered
  3. washwashed with ether
  4. customto yield 5.3 g (80%) of DHK-7-12 as an yellow solid

Sources & evidence

ORD record
ord-1d3bbf140e6d4d0492a1c283c2b5dab3
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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