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Chemistry
Organic Building Blocks
Amines
N-(6-Nitrobenzo[d][1,3]dioxol-5-yl)acetamide
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[ CAS No. 81864-14-4 ] {[proInfo.proName]}

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Chemical Structure| 81864-14-4
Chemical Structure| 81864-14-4
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Product Details of [ 81864-14-4 ]

CAS No. :81864-14-4 MDL No. :MFCD00188397
Formula : C9H8N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 224.17 Pubchem ID :-
Synonyms :

Safety of [ 81864-14-4 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 81864-14-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 81864-14-4 ]

[ 81864-14-4 ] Synthesis Path-Downstream   1~9

YieldReaction ConditionsOperation in experiment
With acetic acid durch Nitrieren;
  • 2
  • [ 108-24-7 ]
  • [ 81864-14-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
Reference： [1]Jones; Robinson [Journal of the Chemical Society, 1917, vol. 111, p. 913]
  • 3
  • [ 13067-19-1 ]
  • [ 81864-14-4 ]
YieldReaction ConditionsOperation in experiment
99% With nitric acid; acetic acid In water at 15 - 20℃; for 16h;
99% With nitric acid In water; acetic acid at 15 - 20℃; for 16h; 158 W-(6-Nitro-1,3-benzodioxol-5-yl)acetamide (219). A solution of 70% HNO3 (15.5 mL, 244 mmol) in HOAc (40 mL) was added dropwise to a stirred solution of acetamide 218 (29.17 g, 163 mmol) in HOAc (150 mL) at 15-20 0C and the mixture stirred at 20 0C for 16 h. The precipitate was filtered, washed with water and dried to give nitroacetamide 219 (36.0 g, 99%) as a yellow powder: mp 207-208 0C (Krasso, A. & Ramuz, H., US Patent 4599347, 1986) mp 212-213 0C]; 1H NMR δ 10.78 (br s, 1 H, NH), 8.36 (s, 1 H, H-7), 7.66 (s, 1 H, H-4), 6.10 (s, 2 H, H-2), 2.27 (s, 3 H, CH3).
86% With nitric acid; acetic acid at 5 - 40℃; for 3h; 1.6.2 (2) N-(6-nitrobenzo[d] [1,3]dioxol-5-yl) acetamide(N-(6-Nitrobenzo[d][1,3]dioxol-5-yl)acetamide ; 10H) After cooling an acetic acid solution (8.5 mL) containing compound 9H (1.30 g, 7.26 mmol) to 5 ° C.,An acetic acid solution (1.5 mL) containing nitric acid (HNO3, 0.49 mL, 10.89 mmol) was added slowly.After stirring at 40 ° C. for 3 hours, the reaction mixture was added to ice water, and the resulting solid was filtered and washed with water to obtain compound 10H (1.40 g, 86%) as a brown solid.
With nitric acid In acetic acid Preparation of the starting material 56.5 g of 5-acetamino-1,3-benzodioxole in 250 ml of glacial acetic acid were nitrated as described above with a solution of 30 ml of nitric acid in 100 ml of glacial acetic acid in a 500 ml sulfonation flask equipped with stirrer, thermometer and dropping funnel. The crystals, removed by filtration under suction, were washed thoroughly with water and dried overnight at about 60° C. in vacuo. There were obtained 68.3 g (96.6% of theory) of 5-acetamino-6-nitro-1,3-benzodioxole of melting point 211°-213° C.

Reference： [1]Hay, Michael P.; Hicks, Kevin O.; Pchalek, Karin; Lee, Ho H.; Blaser, Adrian; Pruijn, Frederik B.; Anderson, Robert F.; Shinde, Sujata S.; Wilson, William R.; Denny, William A. [Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6853 - 6865]
[2]Current Patent Assignee: THE UNIVERSITY OF AUCKLAND - WO2006/104406, 2006, A1 Location in patent: Page/Page column 146
[3]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - KR2020/11270, 2020, A Location in patent: Paragraph 0086; 0292; 0294; 0298-0300
[4]Current Patent Assignee: ROCHE HOLDING AG; SPARAMEDICA - US4435406, 1984, A
  • 4
  • [ 81864-14-4 ]
  • [ 64993-07-3 ]
YieldReaction ConditionsOperation in experiment
97% With sodium ethanolate In methanol for 0.25h; Reflux; 1.6.4 (4) 6-nitrobenzo[d][1,3]dioxol-5-amine (6-Nitrobenzo[d][1,3]dioxol-5-amine; 11H) NaOEt (193 mg, 2.84 mmol) was added into a solution in which compound 10H (200 mg, 0.89 mmol) was dissolved in methanol (4 mL) and stirred at reflux for 15 minutes.After cooling, acetic acid (1.0 mL) was added to the reaction mixture, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1) to obtain Compound 11H (159 mg, 97%) as an orange solid. Got.
80% With sodium methylate In methanol for 0.25h; Reflux;
80% Stage #1: N-(6-Nitrobenzo[d][1,3]dioxol-5-yl)acetamide With sodium methylate In methanol for 0.25h; Heating / reflux; Stage #2: With acetic acid In methanol 158 6-Nitro-1,3-benzodioxol-5-amine (220). NaOMe (4.82 g, 89.2 mmol) was added to a stirred solution of nitroacetamide 219 (5.0 g, 22.3 mmol) in MeOH (100 mL) at reflux temperature and the mixture stirred at reflux temperature for 15 min. HOAc (25 mL, 446 mmol) was added to quench the reaction and the solvent evaporated. Toluene (2 x 50 mL) was added and the azeotrope evaporated. The residue was dissolved in DCM (100 mL) and filtered through a short column of silica to give nitroaniline 220 (3.25 g, 80%) as an orange solid: mp 199-201 0C [lit (Krasso, A. & Ramuz, H., US Patent 4599347, 1986) mp (/PrOH) 203-204 0C]; 1H NMR δ 7.53 (s, 1 H, H-7), 6.30 (br s, 2 H, NH2), 6.22 (s, 1 H, H-4), 5.98 (s, 2 H, H-2).
With sodium methylate In methanol; dichloromethane; acetic acid Preparation of the starting material 40 g of 5-acetamino-6-nitro-1,3-benzodioxole were dissolved with heating in 4 l of methanol in a 10 round flask equipped with a reflux condenser. To this hot solution was added a boiling solution of 40 g of sodium methoxide in 4 l of methanol and the mixture was boiled under reflux for exactly 15 minutes. Then, the reaction was interrupted by adding 220 ml of glacial acetic acid. The methanol was removed by distillation and the last traces thereof, together with the glacial acetic acid, were removed by a two-fold evaporation with toluene. The product went into solution with 3 l of methylene chloride and could be freed from the organic residues by suction filtration. The methylene chloride solution was filtered through silicon dioxide and evaporated in vacuo. The residue, recrystallized from isopropanol, gave 30.9 g (95% of theory) of 5-amino-6-nitro-1,3-benzodioxole of melting point 203°-204° C.

Reference： [1]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - KR2020/11270, 2020, A Location in patent: Paragraph 0086; 0292; 0294; 0304-0306
[2]Hay, Michael P.; Hicks, Kevin O.; Pchalek, Karin; Lee, Ho H.; Blaser, Adrian; Pruijn, Frederik B.; Anderson, Robert F.; Shinde, Sujata S.; Wilson, William R.; Denny, William A. [Journal of Medicinal Chemistry, 2008, vol. 51, # 21, p. 6853 - 6865]
[3]Current Patent Assignee: THE UNIVERSITY OF AUCKLAND - WO2006/104406, 2006, A1 Location in patent: Page/Page column 146
[4]Current Patent Assignee: ROCHE HOLDING AG; SPARAMEDICA - US4435406, 1984, A
  • 5
  • [ 81864-14-4 ]
  • 3-chloro-[1,3]dioxolo[4,5-g][1,2,4]benzotriazine 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.25 h / Heating / reflux 2.1: 100 °C / Neat (no solvent) 2.2: 4 h / 50 - 100 °C 2.3: 3 h / 50 - 100 °C / pH > 7 3.1: trifluoroacetic acid; sodium nitrite / 1 h / 0 - 20 °C 3.2: 1 h / 100 °C 3.3: 0.5 h / 0 °C
Reference： [1]Current Patent Assignee: THE UNIVERSITY OF AUCKLAND - WO2006/104406, 2006, A1
  • 6
  • [ 81864-14-4 ]
  • [1,3]dioxolo[4,5-g][1,2,4]benzotriazin-3-amine 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 0.25 h / Heating / reflux 2.1: 100 °C / Neat (no solvent) 2.2: 4 h / 50 - 100 °C 2.3: 3 h / 50 - 100 °C / pH > 7
Reference： [1]Current Patent Assignee: THE UNIVERSITY OF AUCKLAND - WO2006/104406, 2006, A1
  • 7
  • [ 81864-14-4 ]
  • N1,N1-dimethyl-N2-(1-oxido-[1,3]dioxolo[4,5-g][1,2,4]benzotriazin-3-yl)-1,2-ethanediamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium methylate / methanol / 0.25 h / Heating / reflux 2.1: 100 °C / Neat (no solvent) 2.2: 4 h / 50 - 100 °C 2.3: 3 h / 50 - 100 °C / pH > 7 3.1: trifluoroacetic acid; sodium nitrite / 1 h / 0 - 20 °C 3.2: 1 h / 100 °C 3.3: 0.5 h / 0 °C 4.1: 1,2-dimethoxyethane / 2 h / Heating / reflux
Reference： [1]Current Patent Assignee: THE UNIVERSITY OF AUCKLAND - WO2006/104406, 2006, A1
  • 8
  • [ 81864-14-4 ]
  • N1-(1,4-dioxido-[1,3]dioxolo[4,5-g][1,2,4]benzotriazin-3-yl)-N2,N2-dimethyl-1,2-ethanediamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium methylate / methanol / 0.25 h / Heating / reflux 2.1: 100 °C / Neat (no solvent) 2.2: 4 h / 50 - 100 °C 2.3: 3 h / 50 - 100 °C / pH > 7 3.1: trifluoroacetic acid; sodium nitrite / 1 h / 0 - 20 °C 3.2: 1 h / 100 °C 3.3: 0.5 h / 0 °C 4.1: 1,2-dimethoxyethane / 2 h / Heating / reflux 5.1: dihydrogen peroxide; trifluoroacetic anhydride / dichloromethane; water / 0.25 h / 0 - 20 °C 5.2: 8 h / 0 - 20 °C
Reference： [1]Current Patent Assignee: THE UNIVERSITY OF AUCKLAND - WO2006/104406, 2006, A1
  • 9
  • [ 14268-66-7 ]
  • [ 81864-14-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,4-dioxane / 16 h / 0 - 16 °C 2: nitric acid / water; acetic acid / 16 h / 15 - 20 °C
Multi-step reaction with 2 steps 1: 1,4-dioxane / 1 h / 0 - 20 °C 2: nitric acid; acetic acid / 3 h / 5 - 40 °C
Reference： [1]Current Patent Assignee: THE UNIVERSITY OF AUCKLAND - WO2006/104406, 2006, A1
[2]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - KR2020/11270, 2020, A

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