Hydrochloric Acid → HCID 18414575, compound

HRID 991554Notes

Reaction equation

HRID 991554 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:20])[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:12]O)=[CH:9][C:4]=2[O:3][CH2:2]1.[ClH:21].[H][H]>C(O)C.O.[Pd]>[ClH:21].[ClH:21].[NH2:12][CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)=[O:20]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 136383557HCID 136383557, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18414575HCID 18414575, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Benzo[1,3]dioxol-5-yl-2-pyridin-2-yl-ethane-1,2-dione 2-oxime (2 g, 7.75 mmol) was dissolved in ethanol (100 ml) and hydrochloric acid (2 ml of a 36% solution in water) was added. Palladium on charcoal catalyst (0.5 g) was added and the reaction mixture was stirred under a positive pressure of hydrogen for 1.5 hours. The catalyst was removed by filtration through Kieselguhr and the resulting filtrate evaporated to dryness under reduced pressure. Trituration under anhydrous diethyl ether gave the title compound as a pale yellow solid (1.5 g, 59%); m/z (API) 257 (M+H+, 100%).

Workup

  1. customThe catalyst was removed by filtration through Kieselguhr
  2. customthe resulting filtrate evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7c32451ac9e84964af82e83099e92364
Source dataset
uspto-grants-2002_10
Patent number
US06465493B1

Reaction notes

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