Alternatived Products of [ 16588-15-1 ]
Product Details of [ 16588-15-1 ]
CAS No. : | 16588-15-1 |
MDL No. : | MFCD00088420 |
Formula : |
C7H5ClN2O3
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | SDHXWAPVLOGAJR-UHFFFAOYSA-N |
M.W : |
200.58
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Pubchem ID : | 286562 |
Synonyms : |
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Application In Synthesis of [ 16588-15-1 ]
* 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 [ 16588-15-1 ]
- Downstream synthetic route of [ 16588-15-1 ]
- 1
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[ 16588-15-1 ]
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[ 117821-54-2 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: 1.) NaH / 1.) DMF, room temp., 1 h; 2.) 50 deg C, 5 h
2: H2 / Pd/C / methanol |
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- 2
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[ 2516-96-3 ]
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[ 16588-15-1 ]
Yield | Reaction Conditions | Operation in experiment |
85% |
Stage #1: 2-chloro-5-nitrobenzoic acid With thionyl chloride; N,N-dimethyl-formamide for 3h; Reflux;
Stage #2: With ammonium hydroxide In dichloromethane Cooling with ice; |
44.1
20.157 g 2-Chloro-5-nitrobenzoic acid (100 mmol) was heated at reflux temperature in 100 ml thionyl chloride for 3 hours in the presence of 3 drops of dry N,N-dimethylformamide as catalyst. Reaction mixture was evaporated under reduced pressure and 100 ml dry dichloromethane was added. 100 ml Of 12% NH4OH solution was added dropwise to the ice cold solution and it was stirred for further 2 hours. 400 g ice was then added and it was stirred until the ice melted. Precipitated solid was collected by filtration and washed well with water. The white solid was dried in vacuum desiccator over P2O5. Yield: 17.07 g (85%). Ret. time: 1.93 min., (M+H)+=201, (M+H)-=199; 1HNMR (DMSO-d6, 300 MHz), δ (ppm): 8.24 (bs, 2H), 8.13 (s, 1H), 7.87 (s, 1H), 7.81 (d, J=8.04 Hz, 1H). |
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Multi-step reaction with 2 steps
1: SOCl2 / 3 h / Heating
2: NH4OH / acetone / Ambient temperature |
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Multi-step reaction with 2 steps
1: PCl5
2: diethyl ether; aqueous ammonia |
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Multi-step reaction with 2 steps
1: thionyl chloride
2: water; aqueous ammonia |
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Stage #1: 2-chloro-5-nitrobenzoic acid With thionyl chloride In DMF (N,N-dimethyl-formamide); toluene at 20℃; for 3h; Heating / reflux;
Stage #2: With ammonia In DMF (N,N-dimethyl-formamide); water; toluene Ice cooling; |
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Reference:
[1]Current Patent Assignee: VIROSTATICS - US2014/57911, 2014, A1
Location in patent: Paragraph 0417; 0418
[2]Shinde; Shenoy; Pai
[Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 8, p. 711 - 720]
[3]Montagne
[Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55]
[4]Dey; Doraiswami
[Journal of the Indian Chemical Society, 1933, vol. 10, p. 353,357]
[5]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - EP1176140, 2002, A1
Location in patent: Page 51
- 3
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[ 79-37-8 ]
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[ 2516-96-3 ]
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[ 16588-15-1 ]
Yield | Reaction Conditions | Operation in experiment |
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In dichloromethane |
B 2-Chloro-5-nitrobenzamide
PREPARATION B 2-Chloro-5-nitrobenzamide A mixture of 2-chloro-5-nitrobenzoic acid (15.0 g, 74.0 mmol) in 200 mL of dichloromethane was reacted at 24° C. with oxalyl chloride (16.2 mL, 186.0 mmol) and a catalytic amount of dimethylformamide. After 3 hours, the solvent was removed in vacuo, and the residue was redissolved in 200 mL of fresh dichloromethane. The solution was cooled to 0° C., and ammonia was bubbled into the solution for 5 minutes, whereupon the product precipitated from solution. The product was collected by filtration to yield 6.8 g of 2-chloro-5-nitrobenzamide, mp 174°-175° C.; NMR (DMSO-d6): δ8.2 (m, 2H), 8.2 (s, 1H), 7.8-7.9 (m, 2H). |
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With ammonia In dichloromethane |
24 2-Chloro-5-nitrobenzamide
PREPARATION 24 2-Chloro-5-nitrobenzamide A mixture of 2-chloro-5-nitrobenzoic acid (15.0 g, 74.0 mmol) and 200 mL of dichloromethane was reacted with oxalyl chloride (16.2 mL, 186.0 mmol) and a catalytic amount of dimethylformamide. The mixture was stirred at 25° C. for 3 hours. The solvent was removed in vacuo, and the residue was redissolved in 200 mL of dichloromethane. The solution was cooled to 0° C., and ammonia was bubbled through the cold solution for 5 minutes, whereupon the product precipitated to form solution. The product was collected by filtration to yield 6.8 g, mp 174°-175° C. |
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[ 16588-15-1 ]
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[ 34595-33-0 ]
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[ 16588-15-1 ]
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[ 32188-75-3 ]
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[ 16588-15-1 ]
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[ 288251-82-1 ]
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[ 16588-15-1 ]
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[ 288251-85-4 ]
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[ 16588-15-1 ]
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[ 288251-87-6 ]