HCID 66899822, compound → HCID 53235632, compound

HRID 406903Notes

Reaction equation

HRID 406903 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[N:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 66899822HCID 66899822, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53235632HCID 53235632, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the yellow colored suspension prepared by suspending the compound obtained in Step 4 (19.9 g, 65 mmol) in methanol (200 ml), 10% palladium on carbon (4.0 g) was added. The resulting mixture was subjected to vacuum outgassing and stirred at r.t., for 2 hrs in the flask connected with hydrogen bollum. The resulting mixture was filtered through celite 545 under redued pressure to remove the palladium on carbon. The filterate was concentrated under reduced pressure (reflux condenser, 10 torr, 40). The resulting pale brown colored residue was dissolved in isopropylalcohol (140 ml) and refluxed to dissolve completely. The resulting solution was stood at 0 for 2 hrs to cool, stirred for 30 min and filtered off under redued pressure. The resulting ivory crystalline solid was dried in vacuo to obtain the title compound (15.8 g, 88%).

Workup

  1. customTo the yellow colored suspension prepared
  2. additionwas added
  3. filtrationThe resulting mixture was filtered through celite 545 under redued pressure
  4. customto remove the palladium on carbon
  5. concentrationThe filterate was concentrated under reduced pressure (reflux condenser, 10 torr, 40)
  6. dissolutionThe resulting pale brown colored residue was dissolved in isopropylalcohol (140 ml)
  7. temperaturerefluxed
  8. dissolutionto dissolve completely
  9. waitThe resulting solution was stood at 0 for 2 hrs
  10. temperatureto cool
  11. stirringstirred for 30 min
  12. filtrationfiltered off under redued pressure
  13. customThe resulting ivory crystalline solid was dried in vacuo

Sources & evidence

ORD record
ord-4825e685c28e4a2cb60fc9f9baec528e
Source dataset
uspto-grants-2014_06
Patent number
US08754210B2

Reaction notes

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