Ammonium formate → HCID 23071160, compound

HRID 1351945Notes

Reaction equation

HRID 1351945 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][CH2:19][OH:20])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:20][CH2:19][CH2:18][C:14]1[C:13]2[C:17](=[C:9]([OH:8])[CH:10]=[CH:11][CH:12]=2)[NH:16][CH:15]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 23071124HCID 23071124, compound

Product 1

HCID 23071160HCID 23071160, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(7-(benzyloxy)-1H-indol-3-yl)ethanol (6.31 g, 23.6 mmol) in ethanol (130 mL) are added ammonium formate (6.3 g, 99.9 mmol) and 10% palladium on carbon (50% wet, 555 mg), and the mixture is refluxed for one hour. The reaction solution is cooled to room temperature, and filtered through celite. The solvent is evaporated, and the obtained crude product is purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give 3-(2-hydroxyethyl)-1H-indol-7-ol (3.19 g, 18.0 mmol, yield: 76%).

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. filtrationfiltered through celite
  3. customThe solvent is evaporated
  4. customthe obtained crude product
  5. customis purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3ebe87c238954ba3b02662282d73dee5
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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