HCID 68469477, compound → HCID 58882805, compound

HRID 507378Notes

Reaction equation

HRID 507378 reaction equation
[CH3:1][O:2][C:3]([NH:5][N:6]=[CH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[O:4]>[Pd].C(O)C>[CH3:1][O:2][C:3]([NH:5][NH:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])=[O:4]

Participants

4

Reactant 1

HCID 68469477HCID 68469477, compound

Product 1

HCID 58882805HCID 58882805, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A 50 ml pressure vessel is charged with N′-[3-(2-dimethylamino-ethyl)-1H-indol-5-ylmethylene]hydrazine-carboxylic acid methyl ester (Example 9; 793 mg, 2.74 mmol), ethanol (10.8 ml), and the catalyst (5% Pd/C type E-4522, 158.6 mg). The vessel is sealed and purged with argon (three times), heated in an oil bath to 50° C., and then pressurized with hydrogen (75.4 bar). The stirrer is started (800 rpm), and the hydrogenation allowed to proceed over night. After cooling to ambient temperature the pressure vessel is vented, and the reaction mixture filtered over a pad of Hyflo to remove the catalyst. Removal of the solvent gives the product as a pale yellow residue (707 mg, 88.9%), which is pure by NMR.

Workup

  1. customThe vessel is sealed
  2. custompurged with argon (three times)
  3. waitto proceed over night
  4. temperatureAfter cooling to ambient temperature the pressure vessel
  5. filtrationthe reaction mixture filtered over a pad of Hyflo
  6. customto remove the catalyst
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-455100b879e9414ea1e9a2d224d24c2e
Source dataset
uspto-grants-2010_08
Patent number
US07786156B2

Reaction notes

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