Methanol → Methyl 1-acetyl-4-methoxyindoline-7-acetate

HRID 1884406Notes

Reaction equation

HRID 1884406 reaction equation
[OH2:1].[OH2:2].O.[N+]([O-])([O-])=O.[Tl+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[C:17]([N:20]1[C:28]2[C:23](=[C:24]([O:32][CH3:33])[CH:25]=[CH:26][C:27]=2[C:29](=O)[CH3:30])[CH2:22][CH2:21]1)(=[O:19])[CH3:18].Cl(O)(=O)(=O)=O.[CH3:39]O>>[C:17]([N:20]1[C:28]2[C:23](=[C:24]([O:32][CH3:33])[CH:25]=[CH:26][C:27]=2[CH2:29][C:30]([O:2][CH3:39])=[O:1])[CH2:22][CH2:21]1)(=[O:19])[CH3:18]

Participants

5

Reactant 4

HCID 887MethanolHCID 24247Perchloric AcidHCID 11270721Nitric acid,thallium(3+) salt, trihydrate (9CI)HCID 232464691,7-Diacetyl-4-methoxyindoline

Product 1

HCID 12012755Methyl 1-acetyl-4-methoxyindoline-7-acetateYield 47%

Procedure

Thallium(III) nitrate trihydrate (3.21 g, 7.1 mmol) was added to a solution of 1,7-diacetyl-4-methoxyindoline 22 (1.65 g, 7.1 mmol) in MeOH (70 ml) containing perchloric acid (60% w/w, 1.5 ml) and the mixture was stirred at rt for 4 h. The precipitated white solid was filtered off and the filtrate was concentrated to about 10 ml, diluted with EtOAc (50 ml) and washed with water. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with saturated aq. NaHCO3 and brine, dried and evaporated to give a viscous oil. Flash chromatography [EtOAc-hexanes (4:1)] afforded 23 as white crystals (0.88 g, 47%), mp 80-81° C. (from EtOAc-hexanes) (Found: C, 63.60; H, 6.50; N, 5.28. C14H17NO4 requires C, 63.87; H, 5.51; N, 5.32%); δH (90 MHz) 7.04 (1 H, d, J 8.3, H-5), 6.63 (1 H, d, H-6), 4.06 (2 H, t, J 8.1, H-2), 3.81 (3 H, s, OMe), 3.76 (2 H, s, ArCH2), 3.71 (3 H, s, CO2Me), 2.96 (2 H, t, 3-H) and 2.24 (3 H, s, N-Ac).

Workup

  1. filtrationThe precipitated white solid was filtered off
  2. concentrationthe filtrate was concentrated to about 10 ml
  3. additiondiluted with EtOAc (50 ml)
  4. washwashed with water
  5. extractionThe aqueous phase was extracted with EtOAc
  6. washthe combined organic phases were washed with saturated aq. NaHCO3 and brine
  7. customdried
  8. customevaporated
  9. customto give a viscous oil

Sources & evidence

ORD record
ord-71e71efd5aad4b16a862eac1bc2ae2ab
Source dataset
uspto-grants-2004_07
Patent number
US06765014B1

Reaction notes

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