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ChemicalBook CAS DataBase List 6-nitro-2,3-dihydro-1H-inden-4-amine
860722-19-6

6-nitro-2,3-dihydro-1H-inden-4-amine synthesis

3synthesis methods
Benzoic acid, 4-chloro-3,5-diiodo-

41252-93-1
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6-nitro-2,3-dihydro-1H-inden-4-amine

860722-19-6
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Yield:860722-19-6 37.6%

Reaction Conditions:

with sulfuric acid;nitric acid at -5 - 120; for 2 h;

Steps:

19.2

Step 2: Synthesis of 6-rutro-2 3-dihydro-lH-inden-4-amine (3); To a well stirred solution of N-(2,3-dihydro- l H-inden-4-yl)acetamide (2, 5.5 g, 3 1 .4 mmol) in Cone. Sulfuric acid (23.87 mL) at -5°C was added a cooled mixture of cone. Sulfuric acid (2.36 mL) and nitric acid ( 1.98 mL) slowly enough so that the temperature of the reaction mixture doesn't exceed 0 °C. Whole reaction mixture was added slowly to ice and refluxed at 120 °C for 2 h. Reaction mixture was monitored by TLC and LCMS. After completion of the reaction, reaction mixture was diluted with water, extracted with ethyl acetate. Organic layer was separated, dried and concentrated. Crude product was purified by column chromatography using 6% EtOAc-hexane to afford 6-nitro-2,3-dihydro-l H-inden-4- amine as yellow solid (3, 2.1 g, 37.6%). NMR (400 MHz, CDCI3): δ 7.50 (s, 1 H), 7.38 (s, 1 H), 3.00- 2.80 (t, 2H), 2.80-2.70 (t, 2H), 2.20-2.10 (t, 2H).

References:

WO2011/140338,2011,A1 Location in patent:Page/Page column 91-92