(E)-1-(Benzyloxy)-2-(2-ethoxyethoxy)-4-nitro-5-(2-nitrovinyl)benzene → 6-(2-Ethoxyethoxy)-1H-indol-5-ol

HRID 1427038Notes

Reaction equation

HRID 1427038 reaction equation
C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[N+]([O-])=O)[C:12]([N+:20]([O-])=O)=[CH:11][C:10]=1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH3:28])C1C=CC=CC=1>CO.[C].[Pd]>[CH2:27]([O:26][CH2:25][CH2:24][O:23][C:10]1[CH:11]=[C:12]2[C:13]([CH:15]=[CH:16][NH:20]2)=[CH:14][C:9]=1[OH:8])[CH3:28]

Participants

4

Reactant 1

HCID 86730340(E)-1-(Benzyloxy)-2-(2-ethoxyethoxy)-4-nitro-5-(2-nitrovinyl)benzene

Product 1

HCID 867303416-(2-Ethoxyethoxy)-1H-indol-5-olYield 33%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-carbon (water content, 50%) (6 g) was added to a solution of (E)-1-(benzyloxy)-2-(2-ethoxyethoxy)-4-nitro-5-(2-nitrovinyl)benzene described in Production Example 24-4 (17.5 g, 44.9 mmol) in methanol (180 mL) at room temperature. The reaction liquid was stirred under hydrogen atmosphere at room temperature. After 6 hours, the catalyst was filtered off with celite. The filtrate was concentrated under vacuum and then the residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=2:1-1:1) to obtain the title compound (3.28 g, 33%).

Workup

  1. customThe reaction liquid
  2. filtrationthe catalyst was filtered off with celite
  3. concentrationThe filtrate was concentrated under vacuum
  4. customthe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=2:1-1:1)

Sources & evidence

ORD record
ord-de3e8fc7aeb043c1bc432c58b4bf8b58
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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