Sodium Hydroxide → 3-[3-[[(E)-3-(1,3-Benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid

HRID 2099993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2099993
[OH-].[Na+].C[O:4][C:5](=[O:28])/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15](=[O:27])/[CH:16]=[CH:17]/[C:18]2[CH:26]=[CH:25][C:21]3[O:22][CH2:23][O:24][C:20]=3[CH:19]=2)[CH:9]=1>O1CCCC1>[O:22]1[C:21]2[CH:25]=[CH:26][C:18](/[CH:17]=[CH:16]/[C:15]([NH:14][C:10]3[CH:9]=[C:8](/[CH:7]=[CH:6]/[C:5]([OH:28])=[O:4])[CH:13]=[CH:12][CH:11]=3)=[O:27])=[CH:19][C:20]=2[O:24][CH2:23]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 577968743-[3-[[(E)-3-(1,3-Benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid methyl ester

Produkt 1

HCID 577967883-[3-[[(E)-3-(1,3-Benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(Method G4) 1N NaOH solution (2.56 ml, 2.56 mmol) was added to a solution of 3-[3-[[(E)-3-(1,3-benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid methyl ester (3a) (0.30 g, 0.85 mmol) in tetrahydrofuran (4.0 ml), and the resultant mixture was stirred at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was acidified with 2N HCl solution and extracted with ethyl acetate. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was washed with diethyl ether. The title compound was obtained as a white solid (0.24 g, 84%). 1H NMR (DMSO-d6, HMDSO), δ: 6.09 (2H, s); 6.43 (1H, d, J=16.0 Hz); 6.60 (1H, d, J=16.0 Hz); 6.89-7.76 (8H, m).; 7.92 (1H, br s); 10.16 (1H, br s); 12.38 ppm (1H, br s).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water, saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed
  6. washthe residue was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1995b77634634c31a12f887c591da423
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569724B2

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