Hydrochloric Acid → HCID 67424738, compound

HRID 657707Notes

Reaction equation

HRID 657707 reaction equation
Cl.C(O)C.[NH2:5][C:6]([NH2:33])=[N:7][C:8]([C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:23][CH2:24][O:25]CC3C=CC=CC=3)[C:12]=2[CH:11]=1)=[O:9]>[C].[Pd].C1COCC1>[NH2:33][C:6]([NH2:5])=[N:7][C:8]([C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:23][CH2:24][OH:25])[C:12]=2[CH:11]=1)=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67426271HCID 67426271, compound

Product 1

HCID 67424738HCID 67424738, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 ml portion of 1 M hydrochloric acid and 40 mg of 10% palladium-carbon were added to an ethanol 9 ml-THF 3 ml solution of 393 mg N-(diaminomethylene)-9-[2-(benzyloxy)ethyl]-9H-carbazole-2-carboxamide, followed by stirring at room temperature for 3 days under an atmosphere of hydrogen gas. After carrying out celite filtration by adding 1 M sodium hydroxide aqueous solution, the organic solvent was evaporated and the water layer was extracted with chloroform, followed by washing with saturated brine and drying with anhydrous magnesium sulfate. By evaporating the solvent, 140 mg of N-(diaminomethylene)-9-(2-hydroxyethyl)-9H-carbazole-2-carboxamide was obtained.

Workup

  1. filtrationfiltration
  2. additionby adding 1 M sodium hydroxide aqueous solution
  3. customthe organic solvent was evaporated
  4. extractionthe water layer was extracted with chloroform
  5. washby washing with saturated brine
  6. dry with materialdrying with anhydrous magnesium sulfate
  7. customBy evaporating the solvent

Sources & evidence

ORD record
ord-46f425cd48794807b43c8a83247bbdf3
Source dataset
uspto-grants-2011_12
Patent number
US08076348B2

Reaction notes

Loading…