Acetone → 9-(3,4-Dibromophenyl)-5,6,7,9-tetrahydropyrazolo[5,1-b]quinazolin-8(4H)-one

HRID 1862360Notes

Reaction equation

HRID 1862360 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Br:18])[CH:13]=O.[NH2:19][C:20]1[CH:24]=[CH:23][NH:22][N:21]=1.CC(C)=O>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:2]3[C:1](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=3[NH:19][C:20]3=[CH:24][CH:23]=[N:22][N:21]23)[CH:15]=[CH:16][C:17]=1[Br:18]

Participants

6

Reactant 4

HCID 180AcetoneHCID 104341,3-CyclohexanedioneHCID 6220533,4-DibromobenzaldehydeHCID 178418806HCID 178418806, compound

Product 1

HCID 1355327929-(3,4-Dibromophenyl)-5,6,7,9-tetrahydropyrazolo[5,1-b]quinazolin-8(4H)-oneYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,3-cyclohexanedione (0.11 g, 1 mmol), 3,4-dibromobenzaldehyde (0.26 g, 1 mmol) and 3-aminopyrazole (0.11 g, 1.27 mmol) in ethanol (10 mL) was heated at 80° C. in a sealed 20 mL vial for 3 days. After the reaction mixture was allowed to cool to ambient temperature, the resulting solid was isolated by filtration and recrystallization from acetone to provide 0.23 g (56%) of the title compound.

Sources & evidence

ORD record
ord-2c5b2dd5952e4c7298a92890388d690b
Source dataset
uspto-grants-2003_03
Patent number
US06538000B1

Reaction notes

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