HCID 4777751, compound → HCID 15054039, compound

HRID 1648489Notes

Reaction equation

HRID 1648489 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:18]([NH2:20])=[O:19])[NH:13]2)C1C=CC=CC=1.[H][H]>CO.[Pd].CCCCCC>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:18]([NH2:20])=[O:19])[NH:13]2

Participants

6

Reactant 2

HCID 4777751HCID 4777751, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15054039HCID 15054039, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

4-(benzyloxy)indole-2-carboxamide (4.98 g) in 300 ml of methanol is stirred under 1 atm of hydrogen with 0.75 g of 10% palladium on carbon for 16 hr. The catalyst is filtered off through Celite filter aid, the filtrate concentrated, the residue taken up in ethyl acetate (300 ml) and filtered again. The clear filtrate is concentrated to 200 ml and hexane added to a volume of 450 mi. The cooled solution gives a small amount of gummy, dark material. The filtrate is diluted with hexane and cooled overnight to give a solid. Recrystallization from ethyl acetate/hexane then ethyl acetate gives 4-hydroxyindole-2-carboxamide, mp 219-221.

Workup

  1. filtrationThe catalyst is filtered off through Celite
  2. filtrationfilter aid
  3. concentrationthe filtrate concentrated
  4. filtrationfiltered again
  5. concentrationThe clear filtrate is concentrated to 200 ml and hexane
  6. additionadded to a volume of 450 mi
  7. customThe cooled solution gives a small amount of gummy, dark material
  8. temperaturecooled overnight
  9. customto give a solid
  10. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3640f3b27a8d45fa9845a36aa00b4d9d
Source dataset
uspto-grants-1995_07
Patent number
US05436337

Reaction notes

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