5-hydroxy-6-methoxyindole synthesis

13synthesis methods

Product Name:5-hydroxy-6-methoxyindole
CAS Number:2380-83-8
Molecular formula:C9H9NO2
Molecular Weight:163.17

1-methoxy-5-nitro-4-[(E)-2-nitroethenyl]-2-phenylmethoxybenzene

98258-75-4
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2380-83-8
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Yield:2380-83-8 46%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol;water; for 3 h;

Steps:

1.3 6-Methoxy-1H-indol-5-ol

Production Example 1-3
6-Methoxy-1H-indol-5-ol
(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%).
¹H-NMR Spectrum (CDCl₃) δ (ppm): 3.92 (3H, s), 5.45 (1H, s), 6.39-6.44 (1H, m), 6.88 (1H, s), 7.08 (1H, t, J=2.9 Hz), 7.14 (1H, s), 7.95 (1H, brs).

References:

US2014/235614,2014,A1 Location in patent:Paragraph 0258; 0259; 0260