Dimethylformamide → Methyl 4-dimethylaminovinyl-3-nitrobenzoate

HRID 853718

Reaction equation

HRID 853718 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>CO>[CH3:17][N:18]([CH:20]=[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])[CH3:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 81816Methyl 4-methyl-3-nitrobenzoate

Product 1

HCID 894336Methyl 4-dimethylaminovinyl-3-nitrobenzoateYield 91.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

Into a reaction flask were introduced 89.7 g of methyl 4-methyl-3-nitrobenzoate, 82.1 g of dimethylformamide dimethyl acetal and 200 ml of dimethylformamide (DMF), and the content of the flask was stirred at 120° C. for 6 hours. DMF was distilled off to obtain a red-violet colored solid product. Then, 300 ml of methanol was poured into the flask to wash the crystalline matter, and filtered. Thus, 104.8 g (yield 91%) of methyl 4-dimethylaminovinyl-3-nitrobenzoate was obtained.

Workup

  1. distillationDMF was distilled off
  2. customto obtain a red-violet colored solid product
  3. washto wash the crystalline matter
  4. filtrationfiltered

Sources & evidence

ORD record
ord-dd183e029041473db1d15207a584b189
Source dataset
uspto-grants-2007_08
Patent number
US07255779B2

Linked notes

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