Ammonium formate → Ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate

HRID 629175Notes

Reaction equation

HRID 629175 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:12]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 114836801H-Indole-2-carboxylic acid, 1-methyl-5-(phenylmethoxy)-, ethyl ester

Product 1

HCID 15365972Ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylateYield 239.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of crude ethyl 5-(benzyloxy)-1-methyl-1H-indole-2-carboxylate (1.07 g, 3.46 mmol), 10% palladium on carbon (500 mg, 0.47 mmol) and ammonium formate (1.09 g, 17.29 mmol) in 50 mL ethanol was sparged with argon three times and heated at reflux for 1 h. The mixture was cooled, diluted with 100 mL ethanol and filtered through Celite, washed with ethanol and concentrated to give ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate (1.82 g, 49% over two steps).

Workup

  1. customwas sparged with argon three times
  2. temperatureheated
  3. temperatureat reflux for 1 h
  4. temperatureThe mixture was cooled
  5. additiondiluted with 100 mL ethanol
  6. filtrationfiltered through Celite
  7. washwashed with ethanol
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c9a3786334af4f8ea5b8f3befda8d62a
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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