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

HRID 2276960

Reaktionsgleichung

Reaktionsgleichung von HRID 2276960
[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-1ca3599ba5fa4290b81e83ffaccab756
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133104B2

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