5-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid → 5-Hydroxy-1-isopropyl-1H-indole-2-carboxylic acid

HRID 494005Notes

Reaction equation

HRID 494005 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]([CH3:20])[CH3:19])[C:13]([C:21]([OH:23])=[O:22])=[CH:12]2)C1C=CC=CC=1>[Pd].C(OCC)(=O)C.C(O)C>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:18]([CH3:20])[CH3:19])[C:13]([C:21]([OH:23])=[O:22])=[CH:12]2

Participants

5

Reactant 1

HCID 577407955-Benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid

Product 1

HCID 670735755-Hydroxy-1-isopropyl-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-benzyloxy-1-isopropyl-1H-indole-2-carboxylic acid (41.6 g, 1.0 eq.) and palladium on activated charcoal (10% m:m, 4.3 g, 0.03 eq.) in ethyl acetate (330 mL) and ethanol (235 mL) was flushed with hydrogen, then vigorously stirred for 2 h30 at room temperature. The resulting back suspension was filtered through a dicalite pad. The pad was washed with a mixture of ethyl acetate and ethanol then the liquor was evaporated in vacuo to yield 26.3 g (quant.) of the desired product as off-white oil. MS (m/e): 218.2 (M−H, 100%).

Workup

  1. customwas flushed with hydrogen
  2. filtrationThe resulting back suspension was filtered through a dicalite pad
  3. washThe pad was washed with a mixture of ethyl acetate and ethanol
  4. customthe liquor was evaporated in vacuo

Sources & evidence

ORD record
ord-1775120d512c4bba84e7c52ab4fac81e
Source dataset
uspto-grants-2009_05
Patent number
US07538101B2

Reaction notes

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