Ethyl benzoylacetate → HCID 136409078, compound

HRID 872095Notes

Reaction equation

HRID 872095 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]3[O:13][CH2:14][O:15][C:9]=3[CH:8]=2)=[C:5]([NH2:16])[NH:4][N:3]=1.[C:17]1([C:23](=O)[CH2:24][C:25](OCC)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH2:14]1[O:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]3[C:2]([CH3:1])=[N:3][N:4]4[C:23]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)=[CH:24][C:25](=[O:26])[NH:16][C:5]=34)=[CH:8][C:9]=2[O:15]1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 178434633HCID 178434633, compound

Product 1

HCID 136409078HCID 136409078, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methyl-4-(3,4-methylenedioxyphenyl)-1H-pyrazol-5-amine (300 mg) and ethyl 3-phenyl-3-oxopropanoate (318 mg) are stirred overnight in a pyridine (10 mL) solvent at 95° C. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The extracted organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is distilled under reduced pressure 330 mg of the target compound is yielded by column chromatography.

Workup

  1. customthe reaction solvent is removed by distillation under reduced pressure
  2. extractionThe remainder is extracted with ethyl acetate and water
  3. washThe extracted organic layer is washed with brine
  4. distillationThe dehydrated organic layer is distilled under reduced pressure 330 mg of the target compound
  5. customis yielded by column chromatography

Sources & evidence

ORD record
ord-f354a8fae16c4d73a5dab82711181100
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

Loading…