Acetic Acid → ethyl 7-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate

HRID 1605

Reaktionsgleichung

Reaktionsgleichung von HRID 1605
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([N:12]3[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:14]=[C:13]3[C:22]([O:24]CC)=O)[C:8]2=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:31].C(O)(=O)C>C(#N)C.CO.CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[N:12]4[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:14]=[C:13]4[C:22](=[O:24])[NH:31][C:8]=3[C:9]=2[CH:10]=1

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 19691073Diethyl 1-(6-chloro-1-oxoindan-2-yl)imidazole-2,4-dicarboxylate

Produkt 1

HCID 19691067ethyl 7-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylateAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The procedure is as in Example 1 but starting from 5 g of diethyl 1-(6-chloro-1-oxoindan-2-yl)imidazole-2,4-dicarboxylate, 118 g of ammonium acetate and 190 ml of acetic acid. After washing the precipitate with water and then with methyl ethyl ketone, the solid obtained is first of all ground in acetonitrile and then in methanol and finally in acetone to obtain 2.7 g of ethyl 7-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in the form of a brown solid melting above 260° C. (analysis % calculated C: 58.28, H: 3.67, Cl: 10.75, N: 12.74; % found C: 58.6, H: 3.4, Cl: 10.4, N: 13.1).

Aufarbeitung

  1. washAfter washing the precipitate with water
  2. customwith methyl ethyl ketone, the solid obtained

Quellen und Nachweise

ORD-Eintrag
ord-e4f280544c164e7781c5e91559bf59d4
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726175

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