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Acetic Acid → Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamate

HRID 414697
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 414697
[CH3:1][N:2]([CH3:14])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=1.[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:20]([O:19][C:17](=[O:18])[C:16]([C:15]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([N:2]([CH3:14])[CH3:1])=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 2913524-Dimethylamino-2-nitrobenzaldehyde

Produkt 1

HCID 14365894Ethyl-alpha-carbethoxy-4-dimethylamino-2-nitrocinnamateAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

A mixture of 8.9 grams (g) [50 millimoles (mmol)] of 4-dimethylamino-2-nitrobenzaldehyde [H. Baumann et al, German Pat. No. 2,363,458], 23.7 g (148 mmol) of diethyl malonate, 3.44 g (40.4 mmol) of piperidine and 2.43 g (40.4 mmol) of acetic acid in 400 milliliters (mL) of toluene was refluxed for 16 hours under argon with a Dean Stark trap attached. The solution was cooled to room temperature and washed with 200 mL of 5% aqueous potassium hydroxide (KOH). The organic phase was separated, dried over sodium sulfate (Na2SO4), filtered, and the solvent evaporated. The dark red solid residue was dissolved in 40 mL of methylene chloride (CH2Cl2) and 100 mL of hexane added. After standing for one hour, the solution was filtered to yield 10.4 g of orange crystals. Recrystallization from CH2Cl2 -hexane produced an analytical sample, m.p. 101°-102° C.

Aufarbeitung

  1. washwashed with 200 mL of 5% aqueous potassium hydroxide (KOH)
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. dissolutionThe dark red solid residue was dissolved in 40 mL of methylene chloride (CH2Cl2)
  7. addition100 mL of hexane added
  8. filtrationthe solution was filtered

Quellen und Nachweise

ORD-Eintrag
ord-f62d6b319d524e269bf1037afda2131e
Quelldatensatz
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04794079

Notizen zur Reaktion

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