1-(Benzyloxy)-2-methoxy-4-nitro-5-[(E)-2-nitroethenyl]benzene → 6-Methoxy-1H-indol-5-ol

HRID 1426992Notes

Reaction equation

HRID 1426992 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][CH3:24])C1C=CC=CC=1>CO.[C].[Pd]>[CH3:24][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]

Participants

4

Reactant 1

HCID 131570901-(Benzyloxy)-2-methoxy-4-nitro-5-[(E)-2-nitroethenyl]benzene

Product 1

HCID 1649576-Methoxy-1H-indol-5-olYield 46%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

(E)-1-(Benzyloxy)-2-methoxy-4-nitro-5-(2-nitrovinyl)benzene described in Production Example 1-2 (9.4 g, 28.5 mmol) was suspended in methanol (300 mL), then 10% palladium-carbon (water content, 50%) (3.09 g) was added, and the mixture was stirred under hydrogen atmosphere for 3 hours. The catalyst was filtered off with celite and washed with methanol. The filtrate was concentrated under vacuum and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=3:1-3:7). The target fraction was concentrated under vacuum to obtain the title compound (2.12 g, 46%).

Workup

  1. filtrationThe catalyst was filtered off with celite
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated under vacuum
  4. customthe resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=3:1-3:7)
  5. concentrationThe target fraction was concentrated under vacuum

Sources & evidence

ORD record
ord-f4cdd6d796fd46c98216246c43de0ecc
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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