Dimethylformamide dimethyl acetal → (E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

HRID 1782691Notes

Reaction equation

HRID 1782691 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C)C=O>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:1]/[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 81816Methyl 4-methyl-3-nitrobenzoate

Product 1

HCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 98.3 g (0.504 mol) of methyl 4-methyl-3-nitrobenzoate, 78.0 g (0.655 mol) of N,N-dimethylformamide dimethylacetal and 1 l of dimethylformamide was heated to 140° C. for 3 hours. The solvent was distilled off in vacuo, the residue was triturated thoroughly with 1 l methanol. After drying in vacuo 119.5 g (94.7% of theory) of a red amorphous substance was obtained, which was further processed without any more purification.

Workup

  1. distillationThe solvent was distilled off in vacuo
  2. customthe residue was triturated thoroughly with 1 l methanol
  3. customAfter drying in vacuo 119.5 g (94.7% of theory) of a red amorphous substance
  4. customwas obtained
  5. customwhich was further processed without any more purification

Sources & evidence

ORD record
ord-e2c2cf6c7ccf4edbbce9fe82df963a88
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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