Dimethylformamide → Methyl 4-dimethylaminovinyl-3-nitrobenzoate

HRID 853718

Reaktionsgleichung

Reaktionsgleichung von HRID 853718
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 894336Methyl 4-dimethylaminovinyl-3-nitrobenzoateAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-dd183e029041473db1d15207a584b189
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07255779B2

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