Tetrahydrofuran → Ethyl 4-amino-1-methyl-1H-indole-2-carboxylate

HRID 565018Notes

Reaction equation

HRID 565018 reaction equation
O1CCCC1.[CH3:6][N:7]1[C:15]2[C:10](=[C:11]([N+:16]([O-])=O)[CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>[Pd].CO>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[C:8]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:7]2[CH3:6]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 13401551HCID 13401551, compound

Product 1

HCID 13401554Ethyl 4-amino-1-methyl-1H-indole-2-carboxylateYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a solvent mixture of 50 ml of tetrahydrofuran and 50 ml of methanol was dissolved 1.37 g (5.52 mmol) of ethyl 1-methyl-4-nitro-2-indolecarboxylate. Thereafter 0.30 g of 10% palladium/carbon was added to the solution and catalytic hydrogenation was then conducted at ambient temperature under normal pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 1.2 g (>99%) of ethyl 4-amino-1-methyl-2-indolecarboxylate.

Workup

  1. customwas then conducted at ambient temperature under normal pressure
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was then concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4beba09550b1469db626b8c0dea60c28
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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