beta-Alanine, ethyl ester, hydrochloride → 10-(2-Ethoxycarbonylethylamino)-7-chloro-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dione

HRID 3139

Reaktionsgleichung

Reaktionsgleichung von HRID 3139
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([NH:19]N)=[C:8]3[C:16](=[O:17])[NH:15][NH:14][C:13](=[O:18])[C:9]3=[N:10][C:11]=2[CH:12]=1.Cl.[CH2:22]([O:24][C:25](=[O:29])[CH2:26][CH2:27]N)[CH3:23]>N1C=CC=CC=1.O>[CH2:22]([O:24][C:25]([CH2:26][CH2:27][NH:19][C:7]1[C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:12][C:11]=2[N:10]=[C:9]2[C:13](=[O:18])[NH:14][NH:15][C:16](=[O:17])[C:8]=12)=[O:29])[CH3:23]

Komponenten

5

Edukt 2

HCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 189299057-Chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride

Produkt 1

HCID 1892994110-(2-Ethoxycarbonylethylamino)-7-chloro-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dioneAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 7-chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride (1.0 g, 2.9 mM, as prepared in Example 44) and beta alanine ethyl ester hydrochloride (49.0 g, 320 mM) in pyridine (52 mL) was refluxed for 23 hr. After cooling, the vigorously stirred reaction mixture was diluted slowly with water (100mL) and then filtered to separate a fine red solid. The collected solids were washed with water and chromatographed (eluant: methanol/methylene chloride; 5/95) over silica gel to provide the title ester (0.13 g, 13%) as a red powder, mp 258°-260° C.; MS(CI): 363 (M+H).

Aufarbeitung

  1. temperaturewas refluxed for 23 hr
  2. temperatureAfter cooling
  3. customthe vigorously stirred reaction mixture
  4. filtrationfiltered
  5. customto separate a fine red solid
  6. washThe collected solids were washed with water
  7. customchromatographed (eluant: methanol/methylene chloride; 5/95) over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3dd4f599f9304ea3aa6b0fcf1031451d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733910

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