Ethyl Acetate → 3-methyl-6-nitro-2,3-dihydro-1H-inden-1-one

HRID 593264

Reaction equation

[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[CH2:8]1.C(OCC)(=O)C>S(=O)(=O)(O)O>[CH3:6][CH:7]1[C:15]2[C:10](=[CH:11][C:12]([N+:1]([O-:4])=[O:2])=[CH:13][CH:14]=2)[C:9](=[O:16])[CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

As presented in the following reaction formula, a solution of potassium nitrate (KNO2; 6.2 g, 0.06 mol) in sulfuric acid (30 mL) was added dropwise at 0° C. to a mixture of 3-methyl-2,3-dihydro-1H-inden-1-one (9.0 g, 0.06 mol) in sulfuric acid ic (H2SO4; 40 mL). Then, the mixture was stirred at 0° C. until the completion of reaction. The mixture obtained after the reaction was added to ice water and filtered. The cake was washed with water and purified by silica gel (100 g) column chromatography (product of Merck Co., Ltd.) using an eluent of pentane (PE):ethyl acetate (10:1 (by volume)) to give 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one (8 g, yield: 69%) as a yellow solid.

Workup

customThe mixture obtained after the reaction
filtrationfiltered
washThe cake was washed with water
custompurified by silica gel (100 g) column chromatography (product of Merck Co., Ltd.)

Sources & evidence

ORD record: ord-381802b282e545cfbb890127ce167718
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242928B2

Linked notes

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