Ethyl 5-nitro-1H-indole-2-carboxylate → Ethyl 5-amino-1H-indole-2-carboxylate

HRID 1825001Notes

Reaction equation

HRID 1825001 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2)([O-])=O.C([O-])=O.[NH4+]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2

Participants

6

Reactant 2

HCID 280312Ethyl 5-nitro-1H-indole-2-carboxylateHCID 2723923Ammonium formate

Product 1

HCID 10726872Ethyl 5-amino-1H-indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Under argon, 15 g (60.84 mmol) of ethyl 5-nitro-1H-indole-2-carboxylate are initially charged in 750 ml of ethyl acetate and 750 ml of ethanol. 15.82 g (15.82 mmol) of ammonium formate and 1.50 g of palladium on activated carbon (10%) are added. The mixture is stirred at 90° C. for 30 minutes and then cooled and filtered off through Celite, which is washed with ethyl acetate. The solvent is removed under reduced pressure and the residue is dissolved in chloroform and washed twice with water. The organic phase is dried with sodium sulphate, filtered and concentrated under reduced pressure using a rotary evaporator.

Workup

  1. temperaturecooled
  2. filtrationfiltered off through Celite, which
  3. washis washed with ethyl acetate
  4. customThe solvent is removed under reduced pressure
  5. dissolutionthe residue is dissolved in chloroform
  6. washwashed twice with water
  7. dry with materialThe organic phase is dried with sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customa rotary evaporator

Sources & evidence

ORD record
ord-1503efe3047642b696dfda3f7adb27e2
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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