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Chemistry
Organic Building Blocks
Pyridines
nitropyridine
2,5-Dichloro-4-nitropyridine
Chemistry
Organic Building Blocks
Heterocyclic Building Blocks
Pyridines
Chlorides Nitroes
nitropyridine

[ CAS No. 1400701-63-4 ] {[proInfo.proName]}

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Product Details of [ 1400701-63-4 ]

CAS No. :1400701-63-4 MDL No. :MFCD28648163
Formula : C5H2Cl2N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QVTSUHXJSAHBAB-UHFFFAOYSA-N
M.W : 192.99 Pubchem ID :15740877
Synonyms :

Safety of [ 1400701-63-4 ]

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 [ 1400701-63-4 ]

* 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 [ 1400701-63-4 ]

[ 1400701-63-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1400701-63-4 ]
  • [ 89488-96-0 ]
  • [ 923033-74-3 ]
  • [ 923033-77-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl 2-methyl-5-tetrazolylacetate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: 2,5-dichloro-4-nitropyridine In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #3: With hydrogenchloride In IMS; water for 20h; Heating / reflux; NaH (60% in mineral oil) (1.2 g) was washed with hexane (1OmL); and mixed with stirring with a solution of (2-methyl-2H-tetrazol-5-yl)acetate (3.25 g, see Chθm. Pharm. Bull., 1991, 1099. - contains other tetrazole isomer also) in anhydrous DMF (20 mL) at 20 0C. The mixture was stirred for 2 minutes at 20 0C under argon, whereupon a solution of 2,5-dichloronitropyridine (3.6 g) dissolved in DMF (10 mL) was added in one portion. The EPO mixture turned dark purple and an exotherm was observed. The mixture was stirred for a further 20 minutes, quenched with 2M HCI (5 ml_) and the DMF was removed in vacuo.The residue was dissolved in ethyl acetate (150 mL), washed with 2M HCI (100 ml_), water (100 mL) and brine (100 mL). The solvent was removed in vacuo to give 5.50 g of crude product, which was dissolved in concentrated HCI (25 mL) and IMS (75 mL) and heated under reflux for 20 hours. The mixture was cooled and extracted into DCM (350 mL); the DCM fraction was washed with water (2 x 300 mL) and brine (100 mL). The solvent was removed in vacuo and the resulting oil purified by column chromatography eluting with 6-35% ethyl acetate in hexane give the products that eluted in the order described.5-chloro-2-[(2-methyl-2H-tetrazol-5-yl)methyl]-3-nitropyridine (0.93g, contaminated with tetrazole starting material) Cf6-DMSO δ 8.90 (1 H, d), 8.74 (1 H,d), 4.31 (3H, s), 4.27 (2H, s).5-chloro-2-[(1-methyl-1 H-tetrazol-5-yl)methyl]-3-nitropyridine as a yellow solid (1.2 g,23%) CZ6-DMSO δ 8.85 (1 H, d), 8.77 (1 H, d), 4.90 (2H, s), 3.97 (3H1 s).
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2007/14008, 2007, A2 Location in patent: Page/Page column 19-20
  • 2
  • [ 1400701-63-4 ]
  • [ 1826-67-1 ]
  • [ 1400701-64-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,5-dichloro-4-nitropyridine; vinyl magnesium bromide In tetrahydrofuran at 0 - 20℃; for 1.66667h; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran 23.2 To a solution of vinylmagnesium bromide (54.04 mmol) in tetrahydrofuran (104 mL) was added a solution of the above crude compound (2.98 g, 15.44 mmol) in tetrahydrofuran (100 mL) at 0°C over 40 minutes, and the mixture was stirred at room temperature for 1 hour. To the reaction solution was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, filtered through Phase-separator (Varian Inc.), and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 80:20→50:50) to give 4,7-dichloro-lH-pyrrolo[3,2-c]pyridine (0.74 g, 27%) as a pale yellow powder.APCI-MS m/z: 187/189[M+H]+.
Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - WO2012/124825, 2012, A1 Location in patent: Page/Page column 128
  • 3
  • [ 405230-81-1 ]
  • [ 1400701-63-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,5-dichloro-4-nitropyridine-1-oxide With trichlorophosphate In chloroform Reflux; Stage #2: With sodium hydrogencarbonate In chloroform Cooling with ice; 23.1 To a solution of phosphorus oxychloride (6.40 μ, 73.21 mmol) in chloroform (61.2 mL) was added 2,5-dichloro-4-nitropyridine 1-oxide (3.06 g, 14.64 mmol), and the mixture was stirred under reflux overnight. The reaction solution was poured into ice, adjusted by saturated aqueous sodium hydrogen carbonate solution to pH7 to 8, and extracted with chloroform three times. The organic layer was combined, filtered through Phase-separator (Varian Inc.), and then concentrated under reduced pressure to give a crude 2,5-dichloro-4- nitropyridine (2.98 g, quant.) as a yellow oil.
Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - WO2012/124825, 2012, A1 Location in patent: Page/Page column 128
  • 4
  • [ 1400701-63-4 ]
  • [ 1400701-62-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 1.67 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C
Reference： [1]Current Patent Assignee: MITSUBISHI CHEMICAL HOLDINGS CORPORATION - WO2012/124825, 2012, A1

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Chichibabin Reaction • Chloroalkane Synthesis with SOCI2 • Convert Haloalkanes into Alcohols by SN2 • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Halogenation of Alkenes • Hantzsch Pyridine Synthesis • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Preparation of Amines • Pyridines React with Grignard or Organolithium Reagents • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling
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