Dimethylformamide dimethyl acetal → Methyl 4-dimethylaminovinyl-3-nitrobenzoate

HRID 548219

Reaktionsgleichung

Reaktionsgleichung von HRID 548219
[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=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([CH:1]=[CH:17][N:18]([CH3:20])[CH3:19])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Komponenten

4

Edukt 2

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

Produkt 1

HCID 894336Methyl 4-dimethylaminovinyl-3-nitrobenzoateAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Methyl 4-methyl-3-nitrobenzoate (5 g, 25.6 mmol) was dissolved in DMF (25 mL, 5 vol) and to this was added N,N-dimethylformamide dimethylacetal (4.4 mL, 33.3 mmol). The mixture was allowed to stir at 140° C. for 3 h. The resulting deep red solution was allowed to cool and concentrated under vacuum. The residue was triturated with methanol and filtered. The filtrate was washed with methanol and dried on the sinter to yield 4-(2-dimethylamino-vinyl)-3-nitrobenzoic acid methyl ester (5.2 g, 80%). 1H NMR (300 MHz, DMSO), δ: 2.98 (6H, s, 2×CH3), 3.87 (3H, s, CH3), 5.58 (1H, m, CH), 7.72-7.83 (3H, m, ArH), 8.32 (1H, m, CH).

Aufarbeitung

  1. temperatureto cool
  2. concentrationconcentrated under vacuum
  3. customThe residue was triturated with methanol
  4. filtrationfiltered
  5. washThe filtrate was washed with methanol
  6. customdried on the sinter

Quellen und Nachweise

ORD-Eintrag
ord-cb470447b68142898cc2f7484bf119ce
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939666B2

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