Ammonium formate → HCID 12050028, compound

HRID 1582224Notes

Reaction equation

HRID 1582224 reaction equation
C([O:8][C:9]1[C:10]([CH3:24])=[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>[CH3:18][N:14]1[C:15]2[C:11](=[C:10]([CH3:24])[C:9]([OH:8])=[CH:17][CH:16]=2)[CH:12]=[C:13]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12050027HCID 12050027, compound

Product 1

HCID 12050028HCID 12050028, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 5-benzyloxy-1,4-dimethyl-1H-indole-2-carboxylate (4.00 g, 12.4 mmol), ammonium formate (3.90 g, 61.8 mmol), 10% palladium/carbon (0.20 g) and ethanol (60 ml) was stirred at 60° C. for 1.5 hours. The catalyst was filtered off and the resulting filtrate was concentrated under reduced pressure. A 5% aqueous sodium chloride solution was added to the resulting residue, followed by extraction with ethyl acetate. The extract solution was washed with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 2.89 g of ethyl 1,4-dimethyl-5-hydroxy-1H-indole-2-carboxylate.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. additionA 5% aqueous sodium chloride solution was added to the resulting residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract solution was washed with a 5% aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a661009658b24dd0a28de02c46eff475
Source dataset
uspto-grants-2004_05
Patent number
US06734205B2

Reaction notes

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