HCID 21449076, compound → HCID 21449070, compound

HRID 596881Notes

Reaction equation

HRID 596881 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][C:14]([C:16]3[NH:17][CH:18]=[CH:19][N:20]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([O-])=O.[H][H]>[Pd].CO>[ClH:1].[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][C:14]([C:16]3[NH:20][CH:19]=[CH:18][N:17]=3)=[CH:13][CH:12]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 21449076HCID 21449076, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21449070HCID 21449070, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 17 g (0.057 mole) of the compound of Example I, 200 ml of CH3OH and 1 teaspoon of 5% Pd/C (50% H2O) was shaken on a Parr apparatus with the theoretical amount of hydrogen being absorbed. The mixture was heated to reflux and CH3OH added to dissolution. The catalyst was removed by filtration and the filtrate cooled and diluted with ether. The resulting solid was recrystallized from anhydrous methanol and dried at 110° to yield 7 g (46%). An analytical sample was prepared by drying a sample in the vacuum pistol at the temperature of refluxing dimethylformamide, m.p. 242°-245°.

Workup

  1. customabsorbed
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. additionCH3OH added to dissolution
  5. customThe catalyst was removed by filtration
  6. temperaturethe filtrate cooled
  7. additiondiluted with ether
  8. customThe resulting solid was recrystallized from anhydrous methanol
  9. customdried at 110°
  10. customto yield 7 g (46%)
  11. customAn analytical sample was prepared
  12. dry with materialby drying a sample in the vacuum pistol at the temperature of refluxing dimethylformamide, m.p. 242°-245°

Sources & evidence

ORD record
ord-ec070ec3b79d4c36906492de0152e24c
Source dataset
uspto-grants-1977_03
Patent number
US04012414

Reaction notes

Loading…