ChemicalBook CAS DataBase List 4,5-METHYLENEDIOXY-2-NITROACETOPHENONE

4,5-METHYLENEDIOXY-2-NITROACETOPHENONE synthesis

3synthesis methods

Product Name:4,5-METHYLENEDIOXY-2-NITROACETOPHENONE
CAS Number:56136-84-6
Molecular formula:C9H7NO5
Molecular Weight:209.16

3162-29-6 Synthesis

3162-29-6
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$18.00/5g

56136-84-6
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$45.00/25mg

Yield:56136-84-6 82%

Reaction Conditions:

with HNO₃ in nitromethane at 20; for 2.5 h;

Steps:

XIV

Example XIV; Synthesis of 2-(3,4-methylenedioxy-6-nitrophenyl)-propoxycarbonyl piperidine (FIG. 4A, eq. 4, R=101); Preparation of 3,4-(methylenedioxy)-6-nitroacetophenone. To 3,4-(methylenedioxy)-acetophenone (2.70 g, 17.5 mmol) in 30 mL CH₃NO₂at r.t. was added HNO₃(6.9 mL, 105 mmol) dropwise in 30 min. The solution was stirred for additional 2 h. The reaction mixture was carefully neutralized by the addition of saturated aqueous NaHCO₃solution and then extracted with DCM. The combined organic phase was dried overnight over anhydrous Na₂SO₄. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (eluant: AcOEt/Hex, 1/2, v/v) to afford 3,4-(methylenedioxy)-6-nitroacetophenone (2.80 g, 82%) as light yellow solid. ¹H-NMR (300 MHz, CDCl₃): δ 7.56 (s, 1H, Ar-H), 6.76 (s, 1H, Ar-H), 6.19 (s, 2H, CH₂), 2.50 (s, 3H, CH₃). TLC: 33% ethyl acetate in hexane, Rf=0.5.