Ethyl Acetoacetate → HCID 22387816, compound

HRID 1072779Notes

Reaction equation

HRID 1072779 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1O)([O-])=O.[NH2:14][N:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].[C:32]([O:38][CH2:39][CH3:40])(=[O:37])[CH2:33][C:34]([CH3:36])=O>C(O)C>[CH3:36][C:34]1[C:33]([C:32]([O:38][CH2:39][CH3:40])=[O:37])=[C:25]2[CH:24]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:17]=[CH:16][N:15]2[N:14]=1

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 11430Potassium CarbonateHCID 22388182HCID 22388182, compound

Product 1

HCID 22387816HCID 22387816, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-aminoisonicotinate 2,4-dinitrophenol salt (10.2 g) was suspended in ethanol (147 ml), and potassium carbonate (3.77 g) was added, which was followed by stirring at room temperature for 30 min. To the mixture was added ethyl acetoacetate (3.69 ml), and the mixture was stirred at 60° C. for 5 hr with heating. The insoluble matter was filtered off and the filtrate was concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=7/1) to give the objective compound (2.70 g) as an amber-colored solid.

Workup

  1. stirringthe mixture was stirred at 60° C. for 5 hr
  2. temperaturewith heating
  3. filtrationThe insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-00ec18c89f014e61be3b942ae398d67b
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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