ChemicalBook CAS DataBase List 3,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one

3,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one synthesis

6synthesis methods

Product Name:3,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one
CAS Number:56008-20-9
Molecular formula:C11H15NO
Molecular Weight:177.24

17280-41-0

126-81-8

56008-20-9

Step 1. Synthesis of 3,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one: (E)-acetone aldehyde-1-oxime (0.50 g, 5.74 mmol) and 5,5-dimethyl-1,3-cyclohexanedione (0.80 g, 5.74 mmol) were dissolved in a mixed solvent of acetic acid (35 mL) and water (15 mL). Zinc powder (0.75 g, 11.5 mmol) was slowly added to the reaction system at room temperature. The reaction mixture was refluxed under stirring conditions. After completion of the reaction, the reaction solution was concentrated under reduced pressure and subsequently extracted with dichloromethane and saturated brine. The pH of the aqueous phase was adjusted with saturated sodium bicarbonate solution to 6. The aqueous phase was again extracted with dichloromethane and the organic layers were combined and dried over anhydrous magnesium sulfate. After filtration to remove the desiccant, the filtrate was concentrated under reduced pressure to give the crude product. Purification of the crude product by silica gel column chromatography (eluent: hexane/ethyl acetate, 1/3) afforded 3,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one as a yellow solid (4.9 g, 52% yield).

17280-41-0 Synthesis

17280-41-0
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126-81-8 Synthesis

126-81-8
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56008-20-9
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Yield:56008-20-9 52%

Reaction Conditions:

with acetic acid;zinc in water;Reflux;

Steps:

45.1 Step 1. Synthesis of 3,6,6-trimethyl-6,7-dihydro-lH-indole-4(5H)-on [formula 6-2]

Step 1. Synthesis of 3,6,6-trimethyl-6,7-dihydro-lH-indole-4(5H)-on [formula 6-2]Anti-pyruvic aldehyde- 1-oxime [formula 6-1] (0.50 g, 5.74 mmol) and 5,5-dimethyl- 1,3-cyclohexandion [formula 6-7] (0.80 g, 5.74 mmol) were dissolved in acetic acid (35 mL) and H₂0 (15 mL) . Thereto, zinc powder (0.75 g, 11.5 mmol) was added slowly maintaining room temperature. The reaction mixture was refluxed with stirring, concentrated under reduced pressure and extracted with CH₂C1₂ and brine, of which pH was adjusted to 6 using saturated NaHC0₃. The reaction mixture was extracted with CH₂C1₂; organic layer was dried over anhydrous MgS0₄ and filtered. Residue was concentrated under reduced pressure and purified by column chromatography (Si0₂; hexane/ethylacetate, 1/3) to yield the title compound as yellow solid (4.9 g, 52 %).

References:

WO2013/62344,2013,A1 Location in patent:Page/Page column 87

126-81-8 Synthesis

126-81-8
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306-44-5 Synthesis