5-Nitroindole → 3-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole

HRID 1198188Notes

Reaction equation

HRID 1198188 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].BrC[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27]>O1CCOCC1.[Ag]=O>[CH3:27][O:26][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:16]=1[CH2:15][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][CH:8]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 2

HCID 225235-NitroindoleHCID 54171960Methyl 4-bromoethyl-3-methoxybenzoate

Product 1

HCID 114732633-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindoleYield 55.6%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Silver oxide (2.32 grams) was added to a solution of 5-nitroindole (1.62 grams) and methyl 4-bromoethyl-3-methoxybenzoate (2.6 grams) in 10 mL of dioxane. The mixture was heated at 60° for 20 hours. The dioxane was evaporated and ethyl acetate was added to the residue. The resulting suspension was filtered. The filtrate was evaporated and the residue was purified on silica with hexane/ethyl acetate to give 1.8 grams of title compound, m.p. 162°-163°.

Workup

  1. temperatureThe mixture was heated at 60° for 20 hours
  2. customThe dioxane was evaporated
  3. additionethyl acetate was added to the residue
  4. filtrationThe resulting suspension was filtered
  5. customThe filtrate was evaporated
  6. customthe residue was purified on silica with hexane/ethyl acetate

Sources & evidence

ORD record
ord-ce1681b5c4e74217aea779480d0dc437
Source dataset
uspto-grants-1994_01
Patent number
US05280039

Reaction notes

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