Dimethylformamide dimethyl acetal → (E)-methyl 4-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoate

HRID 14167Notes

Reaction equation

HRID 14167 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>C1(C)C=CC=CC=1>[CH3:20][N:21]([CH3:23])/[CH:22]=[CH:1]/[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 4366501Methyl 4-methyl-3,5-dinitrobenzoate

Product 1

HCID 11587426(E)-methyl 4-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoateYield 99.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of methyl 4-methyl-3,5-dinitrobenzoate (5.6 g) in toluene (20 mL) was added dimethylformamide dimethyl acetal (4.17 g) and 5-sulfo salycylic acid hydrate (0.1 g). The mixture was heated to 110° C. for 19 h, removed from heat and cooled to room temperature. The solvents were removed under reduced pressure at which time hexanes was added to the residue and the residue was filtered to give 6.85 g of the title compound: 1H NMR (CDCl3) δ 2.97, 3.96, 5.54, 6.74, 8.33.

Workup

  1. customremoved
  2. temperaturefrom heat
  3. temperaturecooled to room temperature
  4. customThe solvents were removed under reduced pressure at which time hexanes
  5. additionwas added to the residue
  6. filtrationthe residue was filtered

Sources & evidence

ORD record
ord-9d6648b3bd074412b01bcbe56dcf4f47
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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