Ethyl Acetoacetate → HCID 22642453, compound

HRID 973388Notes

Reaction equation

HRID 973388 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH2:13][C:12](=[O:14])[N:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:21](OCC)(=[O:26])[CH2:22][C:23]([CH3:25])=O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:21](=[O:26])[CH:22]=[C:23]([CH3:25])[C:13]3[C:12](=[O:14])[N:11]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:10][C:9]2=3)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 178516404HCID 178516404, compound

Product 1

HCID 22642453HCID 22642453, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

To 5.7 g of 3-(3-chlorophenylamino)-1-phenyl-2-pyrazolin-5-one were added 30 ml of acetic acid and 4 g of ethyl acetoacetate and the solution was heated at a bath temperature of 150° C. for 10 hours and 20 minutes while stirring. Any insoluble matter was collected by filtration while hot, washed with isopropanol, and air-dried to obtain 2.3 g of 7-(3-chlorophenyl)-2-phenyl-4-methylpyrazolo[3,4-b]pyridine-3,6-dione having a melting point of 278° to 282° C.

Workup

  1. filtrationAny insoluble matter was collected by filtration while hot,
  2. washwashed with isopropanol
  3. customair-dried

Sources & evidence

ORD record
ord-b81db817026544da92329d8fc65bd840
Source dataset
uspto-grants-1991_11
Patent number
US05063146

Reaction notes

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