Triethylamine → 5-(2-Benzyloxy-ethoxy)-1,3-dihydro-indol-2-one

HRID 1955256Notes

Reaction equation

HRID 1955256 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:22]([O-])=O)=[C:16]([CH2:18][C:19](O)=[O:20])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>[Pd].CO.C(O)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]2[C:15](=[CH:14][CH:13]=1)[NH:22][C:19](=[O:20])[CH2:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 23294499[5-(2-Benzyloxy-ethoxy)-2-nitro-phenyl]-acetic acid

Product 1

HCID 232942795-(2-Benzyloxy-ethoxy)-1,3-dihydro-indol-2-oneYield 79%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of [5-(2-benzyloxy-ethoxy)-2-nitro-phenyl]-acetic acid (0.58 g, 1751 mmol), 5% palladium on carbon (0.05 g) and triethylamine (0.37 ml, 2.66 mmol) in methanol (35 ml) was stirred under a hydrogen atmosphere (1 atm) for 3 h. After removal of the catalyst by filtration, the filtrate was evaporated to give a yellow oil. The oil was dissolved in 10 ml of acetic acid and the solution was stirred at 80° C. under argon for 3 h. The acetic acid was removed on a rotavap. The residue was dissolved in a small amount of methylene chloride and chromatographed on silica gel eluted with 30% ethyl acetate in methylene chloride to give 5-(2-benzyloxy-ethoxy)-1,3-dihydro-indol-2-one (0.39 g, 79%) as a white solid. Analysis calculated for C17H17NO3 : C, 72.07; H, 6.05; N, 4.85. Found: C, 72.09; H, 6.01; N, 4.85.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe filtrate was evaporated
  4. customto give a yellow oil
  5. stirringthe solution was stirred at 80° C. under argon for 3 h
  6. customThe acetic acid was removed on a rotavap
  7. dissolutionThe residue was dissolved in a small amount of methylene chloride
  8. customchromatographed on silica gel
  9. washeluted with 30% ethyl acetate in methylene chloride

Sources & evidence

ORD record
ord-14e74948d82949caa0ec653cfef2aa52
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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