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[ CAS No. 67984-81-0 ]

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Chemical Structure| 67984-81-0
Chemical Structure| 67984-81-0
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CAS No. :67984-81-0 MDL No. :MFCD02261930
Formula : C7H5NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :135.12 g/mol Pubchem ID :3017820
Synonyms :

Safety of [ 67984-81-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67984-81-0 ]

  • Upstream synthesis route of [ 67984-81-0 ]
  • Downstream synthetic route of [ 67984-81-0 ]

[ 67984-81-0 ] Synthesis Path-Upstream   1~12

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YieldReaction ConditionsOperation in experiment
56 g With aluminum (III) chloride; triethylamine In toluene at 70 - 75℃; for 8 h; Example 1 Preparation of 2,3-dihydroxy benzoic acid form 2,3-dimethoxy benzoic acid [0069] To a stirred solution of 2,3-dimethoxy benzoic acid (100 g; 0.549 mol) in dichloromethane (500 mL) and catalytic amount of DMF (2 mL) at a temperature about 30-35° C., thionyl chloride (130.6 g; 1.102 mol) was added and stirred for a period of two hours. Reaction was monitored by TLC for completion of the starting material (NMT-5percent). If reaction not completed added thionyl chloride (9.8 g; 0.823 mol). Upon completion of reaction, the reaction mass was quenched in to the −5° C. chilled aqueous ammonia (580 mL) solution at a temperature below 15° C. under stirring. The reaction mass was stirred at temperature 30-35° C. over a period of 30 min. The separated organic fraction was concentrated under atmospheric distillation at below 50° C., charged toluene (100 ml) and co-distilled until the reaction mass moisture content become less than 0.5percent. The obtained benzamide compound was dissolved in toluene (500 mL) at temperature about 30-35° C. To the reaction mass was added POCl3 (126.3 g; 0.824 mol). The temperature of the reaction mass was raised to 80-85° C. and maintained over a period of 1-2 hours for the completion of the reaction (Progress of the reaction was monitored by HPLC until the benzamide NMT 1.0percent). If the reaction was not completed, added second lot of POCl3 (10.1 g; 0.06 mol) at 30-35° C. The reaction mass was cooled to a temperature about 30-35° C. upon completion of the reaction. The reaction mixture was added to cold water (1000 mL) at 0-5° C. The organic fraction was separated and washed with 8percent sodium bicarbonate solution. The organic fraction was separated and azeotropic distilled at 110-115° C. (until moisture content NMT 0.2percent), after reaching moisture content to normal limit cooled the reaction mass temperature to 40° C. and distilled reaction mass volume becomes 3 volumes under vacuum at a temperature 40-50° C. After distillation cooled the reaction mass temperature to 30-35° C. In another RB flask charged toluene (160 ml), triethyl amine (199.7 g; 1.977 mol) at 30-35° C. and stirred for 10 min. charged aluminum chloride (52.7 g×5; 1.977 mol) in five lots with the gap of 10 min between each lot addition (addition of aluminum chloride may raise the temperature to 45-50° C.). The reaction mass temperature was raised to about 70-75° C. and added above reaction mass (methoxy compound) for 30 min. maintained the reaction mass at 70-75° C. for 8 hr. Progress of the reaction was monitored by HPLC (until the 2,3-dimethoxybenzonitrile content 0.25percent and 3-methoxy-2-hydroxybenzonitrile content 0.2percent). If reaction was not completed added second lot of triethyl amine (27.7 g; 0.27 mol) and aluminum chloride (36.6 g; 0.27 mol). Upon completion of the reaction, the reaction mixture was cooled to 30-35° C. and quenched with chilled aqueous HCl (prepared by addition of water (500 ml) and Conc. HCl (500 ml)) at 15° C. Stirred reaction mass at 25-30° C. for about 30 min, filtered the obtained solids and separated aqueous and organic layers. Charged MIBK (320 ml) to the solids and charged above aqueous layer, filtered through celite and separated aqueous and organic layers. To the aqueous layer given MIBK (320+160 ml) extractions. To the combined organic layer given 20percent sodium chloride solution washing, organic layer was azeotropic distilled at 110° C. to remove the water (moisture content NMT 0.2percent). Cooled the reaction mass temperature to 30° C. and filtered through 0.45 micron/1 micron filter. To the filterate charged 1percent EDTA (400 ml), stirred for 30 min and filtered through 10 micron cloth. The organic fraction was separated and distilled off to obtain the residue. The residue was treated with dichloromethane (400 ml) and the solid obtained was filtered and dried under vacuum over 6 hr at 60-65° C. to obtain the title compound 2,3-dihydroxy benzonitrile. (56 g, yield 75.4percent) [0070] Purity by HPLC 99.81percent; [0071] Impurity A: 0.05percent [0072] Impurity B: 0.07percent
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 821 - 831
[2] Patent: WO2014/13512, 2014, A1, . Location in patent: Page/Page column 10; 12
[3] Patent: US2015/175532, 2015, A1, . Location in patent: Paragraph 0069-0072
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Reference: [1] European Journal of Organic Chemistry, 2006, # 11, p. 2513 - 2516
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Reference: [1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 4-5, p. 727 - 739
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Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1881 - 1894
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Reference: [1] Chemical and Pharmaceutical Bulletin, 2010, vol. 58, # 11, p. 1552 - 1553
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Reference: [1] Patent: WO2014/13512, 2014, A1,
[2] Patent: US2015/175532, 2015, A1,
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Reference: [1] Patent: WO2014/13512, 2014, A1,
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Reference: [1] Patent: WO2014/13512, 2014, A1,
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Reference: [1] Chemistry Letters, 1999, # 3, p. 197 - 198
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Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958, vol. 246, p. 784,787
[2] Acta polytech. scand. chem. Ser., 1960, # 6, p. 76
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Reference: [1] Chemistry Letters, 1999, # 3, p. 197 - 198
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Reference: [1] Chemistry Letters, 1999, # 3, p. 197 - 198
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