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

HRID 1605

Reaction equation

HRID 1605 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

HCID 19691067ethyl 7-chloro-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylateYield 61.7%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-e4f280544c164e7781c5e91559bf59d4
Source dataset
uspto-grants-1998_03
Patent number
US05726175

Linked notes

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