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Structure of 79134-11-5

Chemical Structure| 79134-11-5

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Product Details of [ 79134-11-5 ]

CAS No. :79134-11-5
Formula : C6H6N2O4S
M.W : 202.19
SMILES Code : O=[N+](C1=CN=C(S(=O)(C)=O)C=C1)[O-]
MDL No. :MFCD00847293

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Application In Synthesis of [ 79134-11-5 ]

* 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.

  • Upstream synthesis route of [ 79134-11-5 ]
  • Downstream synthetic route of [ 79134-11-5 ]

[ 79134-11-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 79134-11-5 ]
  • [ 187143-22-2 ]
YieldReaction ConditionsOperation in experiment
91% With iron; ammonium chloride In methanol; water for 1 h; Reflux Preparation 156-Methylsulfonylpyridin-3 -amineDissolve 2-(methylsulfonyl)-5-nitropyridine (1.80 g, 8.90 mmol) in water (25 mL) and methanol (25 mL). Add iron (1.49 g, 26.68 mmol), and ammonium chloride (2.86 g, 53.47 mmol). Stir for 1 h at reflux temperature. Filter the mixture, washing with EtOAc. Extract the filtrate with EtOAc. Dry the organic portion over MgS04; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to afford the title compound (1.40 g, 91percent). LC-ES/MS m/z 173 [M+H]+.
86% With hydrogen In methanol; ethyl acetate for 3 h; A suspension of 241 mg (0.34 mmol) of 20percent of Pearlman's catalyst on carbon and 693 mg (3.43 mmol) of the 2-methanesulfonyl-5-nitropyridine in 15 mL of MeOH and 3 mL of ethyl <n="61"/>acetate was stirred under an atmosphere of hydrogen for 3 hours. The solution was filtered and concentrated. The crude mixture was further purified by filtration through a silica column with ethyl acetate to afford 510 mg (86percent) of 6-methanesulfonylpyridin-3-ylamine.
70.5%
Stage #1: With acetic acid In water for 2 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 0.5 h;
Preparation of 3-Amino-6-(methylsulfonyl)pyridine From 3-Nitro-6-(methylsulfonyl)pyridine
3-Nitro-6-(methylsulfonyl)pyridine (10 g, 49.5 mmol) was suspended in water (200 mL).
Iron powder (5.0 g, 89.3 mmol) and acetic acid (0.5 mL) were added to the above mixture.
The mixture, which resulted, was heated to reflux for 2 h.
The reaction was monitored by TLC (EtOAc/hexane, 1/1).
The reaction mixture was then cooled to rt and a saturated solution of NaHCO3 (100 mL) was added to the mixture.
Ethyl acetate (200 mL) was added to the above mixture and the mixture which resulted was stirred at rt for 30 min.
The mixture was filtered through celite and the organic layer was collectd.
The aqueous layer was extracted with ethyl acetate (200 mL*3).
The organic extractions were combined and dried (NaSO4).
The solvent was removed under reduced pressure to provide the 3-amino-6-(methylsulfonyl)pyridine (6 g, 70.5percent).
References: [1] Patent: WO2013/66640, 2013, A1, . Location in patent: Page/Page column 19.
[2] Patent: WO2009/149139, 2009, A1, . Location in patent: Page/Page column 58-59.
[3] Patent: US6649636, 2003, B1, . Location in patent: Page/Page column 52.
[4] Journal of the Chemical Society, &lt;1948&gt; 1939, 1944, .
[5] Patent: WO2004/48367, 2004, A1, . Location in patent: Page 11.
  • 2
  • [ 79134-11-5 ]
  • [ 7439-89-6 ]
  • [ 187143-22-2 ]
YieldReaction ConditionsOperation in experiment
70.5% With acetic acid In water; ethyl acetate Step 3
3-AMINO-6-(METHYLSULFONYL)PYRIDINE
3-Nitro-6-(methylsulfonyl)pyridine (10 g, 49.5 mmol) was suspended in water (200 mL).
Iron powder (5.0 g, 89.3 mmol) and acetic acid (0.5 mL) were added to the above mixture.
The mixture, which resulted, was heated to reflux for 2 hours.
The reaction was monitored by thin layer chromatography (ethyl acetate/hexane, 1/1).
The reaction mixture was then cooled to room temperature and a saturated solution of sodium bicarbonate (NaHCO3) (100 mL) was added to the mixture.
Ethyl acetate (200 mL) was added to the above mixture and the mixture, which resulted, was stirred at room temperature for 30 minutes.
The mixture was filtered through Celite.(R). and the organic layer was collected.
The aqueous layer was extracted with ethyl acetate (200 mL*3).
The organic extractions were combined and dried over sodium sulfate.
The solvent was removed under reduced pressure to provide the 3-amino-6-(methylsulfonyl)pyridine (6 g, 70.5percent).
70.5% With acetic acid In water; ethyl acetate Step 3
3-Amino-6-(Methylsulfonyl)Pyridine
3-Nitro-6-(methylsulfonyl)pyridine (10 g, 49.5 mmol) was suspended in water (200 mL).
Iron powder (5.0 g, 89.3 mmol) and acetic acid (0.5 mL) were added to the above mixture.
The mixture, which resulted, was heated to reflux for 2 hours.
The reaction was monitored by thin layer chromatography (ethyl acetate/hexane, 1/1).
The reaction mixture was then cooled to room temperature and a saturated solution of sodium bicarbonate (NaHCO3) (100 mL) was added to the mixture.
Ethyl acetate (200 mL) was added to the above mixture and the mixture which resulted was stirred at room temperature for 30 minutes.
The mixture was filtered through Celite.(R). and the organic layer was collected.
The aqueous layer was extracted with ethyl acetate (200 mL*3).
The organic extractions were combined and dried over sodium sulfate.
The solvent was removed under reduced pressure to provide the 3-amino-6-(methylsulfonyl)pyridine (6 g, 70.5percent).
70.5% With acetic acid In water; ethyl acetate Step 3
3-AMINO-6-(METHYLSULFONYL)PYRIDINE
3-Nitro-6-(methylsulfonyl)pyridine (10 g, 49.5 mmol) was suspended in water (200 mL).
Iron powder (5.0 g, 89.3 mmol) and acetic acid (0.5 mL) were added to the above mixture.
The mixture, which resulted, was heated to reflux for 2 hours.
The reaction was monitored by thin layer chromatography (ethyl acetate/hexane, 1/1).
The reaction mixture was then cooled to room temperature and a saturated solution of sodium bicarbonate (NaHCO3) (100 mL) was added to the mixture.
Ethyl acetate (200 mL) was added to the above mixture and the mixture which resulted was stirred at room temperature for 30 minutes.
The mixture was filtered through Celite.(R). and the organic layer was collected.
The aqueous layer was extracted with ethyl acetate (200 mL*3).
The organic extractions were combined and dried over sodium sulfate.
The solvent was removed under reduced pressure to provide the 3-amino-6-(methylsulfonyl)pyridine (6g, 70.5percent).
References: [1] Patent: US2002/58681, 2002, A1, .
[2] Patent: US6506779, 2003, B1, .
[3] Patent: US6531492, 2003, B1, .
 

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