Malononitrile → 2-amino-3-cyano-7-ethoxy-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene

HRID 1071869

Reaktionsgleichung

Reaktionsgleichung von HRID 1071869
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[C:14](#[N:18])[CH2:15][C:16]#[N:17].N1CCCCC1.[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1)[CH3:26]>C(O)C>[NH2:17][C:16]1[O:34][C:30]2[C:31]([CH:7]([C:6]3[CH:5]=[C:4]([O:10][CH3:11])[C:3]([O:12][CH3:13])=[C:2]([Br:1])[CH:9]=3)[C:15]=1[C:14]#[N:18])=[CH:32][CH:33]=[C:28]([O:27][CH2:25][CH3:26])[CH:29]=2

Komponenten

6

Edukt 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 693063-EthoxyphenolHCID 813793-Bromo-4,5-dimethoxybenzaldehyde

Produkt 1

HCID 223953192-amino-3-cyano-7-ethoxy-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a mixture of 5-bromoveratraldehyde (245 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) in ethanol (2 ml) was added piperidine (0.1 ml, 1 mmol). The mixture was stirred at room temperature for 15 min, then 3-ethoxyphenol (138 mg, 1 mmol) was added and it was stirred overnight. The solvent was evaporated and the residue was purified by chromatography on silica gel (EtOAc/Hexane, 1:2) to yield the title compound. 1H NMR (CDCl3): 6.84-6.82 (m, 2H), 6.70 (s, 1H), 6.61-6.65 (m, 1H), 6.53 (s, 1H), 4.62 (m, 3H), 4.0 (q, J=6.0, 2H), 3.82 (s, 6H), 1.4 (t, J=6.0, 3H).

Aufarbeitung

  1. stirringit was stirred overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on silica gel (EtOAc/Hexane, 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-7a9549c01fd84a6dbfc3663fb41b1e69
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906203B1

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