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Chemical Structure| 61563-28-8 Chemical Structure| 61563-28-8

Structure of 61563-28-8

Chemical Structure| 61563-28-8

2-Chloro-3-methylbenzaldehyde

CAS No.: 61563-28-8

4.5 *For Research Use Only !

Cat. No.: A131367 Purity: 95%

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Product Details of [ 61563-28-8 ]

CAS No. :61563-28-8
Formula : C8H7ClO
M.W : 154.59
SMILES Code : O=CC1=CC=CC(C)=C1Cl
MDL No. :MFCD11845907
Boiling Point : No data available
InChI Key :LGOLMLQWRYFRHP-UHFFFAOYSA-N
Pubchem ID :14492779

Safety of [ 61563-28-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 61563-28-8 ]

* 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 [ 61563-28-8 ]

[ 61563-28-8 ] Synthesis Path-Downstream   1~34

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  • [ 102626-21-1 ]
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YieldReaction ConditionsOperation in experiment
91.4% A solution of DCM (30 ML) was cooled TO-78C and oxalyl chloride (1.34 ml, 15. 2MMOL, 1.2eq) was added under nitrogen followed by dropwise addition of DMSO (2.2 ml, 31.7mmol, 2. 5EQ) in DCM (10ml). After stirring for 15 min a solution of 2- chloro-3-methylbenzylalcohol (2g, 12.7mmol, leq) in DCM (12 ml) was added dropwise. After a further 30 min triethylamine (9.03 ml, 63. 5MMOL, 5EQ) was added in one portion and the mixture warmed to room temperature over 1 hour. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate (50 ml) and the aqueous layer extracted with DCM (2 x 50 ml). The combined organic extracts were dried (MGS04) and the solvent removed in vacuo to give 2-chloro-3-methylbenzaldehyde (1.8g, 91.4%) as a yellow oil; 1H NMR (300 MHz, CDC13) 8= 10. 53 (1H, s, CHO), 7.81- 7.74 (1H, m, ArH), 7.53-7. 46 (1H, m, ArH), 7.34-7. 23 (1H, m, ArH) and 2.46 (3H, s).
With manganese(IV) oxide; In dichloromethane; at 25℃; for 12h;Inert atmosphere; To a solution of (2-chloro-3-methyl-phenyl)methanol (26.2 g, 167 mmol) in dichloromethane (350 mL) was added manganese dioxide (116 g, 1.34 mol) under nitrogen. After the addition, the reaction mixture was stirred at 25 C for 12 hrs. The solid was filtered, and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (eluted with petroleum ether:ethyl acetate = 20:1) to give the title compound.1H NMR (400MHz, DMSO-d6) delta = 10.42 - 10.34 (m, 1H), 7.68 (t, J = 8.2 Hz, 2H), 7.42 (t, J = 7.5 Hz, 1H), 2.39 (s, 3H)
With manganese(IV) oxide; In dichloromethane; at 25℃; for 12h;Inert atmosphere; Step 2 - 2-Chloro-3-methylbenzaldehyde (0337) [00250] To a solution of (2-chloro-3-methyl-phenyl)methanol (26.2 g, 167 mmol) in dichloromethane (350 mL) was added manganese dioxide (116 g, 1.34 mol) under nitrogen. After the addition, the reaction mixture was stirred at 25 C for 12 hrs. The solid was filtered, and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (eluted with petroleum ether:ethyl acetate = 20:1) to give the title compound.1H NMR (400MHz, DMSO-d6) delta = 10.42 - 10.34 (m, 1H), 7.68 (t, J=8.2 Hz, 2H), 7.42 (t, J=7.5 Hz, 1H), 2.39 (s, 3H).
With manganese(IV) oxide; In dichloromethane; at 20℃; for 12h;Inert atmosphere; To a solution of (2-chloro-3-methyl-phenyl)methanol (26.2 g, 167 mmol) in dichloromethane (350 mL) was added manganese dioxide (116 g, 1.34 mol) under nitrogen. After, the reaction mixture was stirred at rt for 12 hrs. The solid was filtered, and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (eluted with petroleum ethenethyl acetate = 20: 1) to give the title compound. NMR (400MHz, DMSO-d5) delta = 10.42 - 10.34 (m, 1H), 7.68 (t, J = 8.2 Hz, 2H), 7.42 (t, J= 7.5 Hz, 1H), 2.39 (s, 3H).

YieldReaction ConditionsOperation in experiment
EXAMPLE 9 2-Chloro-3-methylbenzoic acid was reduced by treating with diborane in tetrahydrofuran and the resulting 2-chloro-3-methylbenzyl alcohol was oxidized with activated magnesium dioxide in methylene chloride to give 2-chloro-3-methylbenzaldehyde.
  • 6
  • [ 1816-92-8 ]
  • [ 61563-28-8 ]
  • methyl 2-azido-3-(2-chloro-3-methylphenyl)acrylate [ No CAS ]
  • 8
  • [ 61563-28-8 ]
  • [ 50536-56-6 ]
  • 9
  • [ 61563-28-8 ]
  • C10H7Cl2NO [ No CAS ]
  • 10
  • [ 61563-28-8 ]
  • C10H9ClN2O [ No CAS ]
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  • [ 61563-28-8 ]
  • C15H15ClN2O2 [ No CAS ]
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  • [ 61563-28-8 ]
  • C15H13Br2ClN2O2 [ No CAS ]
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  • C15H13ClN2O3 [ No CAS ]
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  • [ 61563-28-8 ]
  • C47H41F3N8OS [ No CAS ]
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  • [ 61563-28-8 ]
  • 4-chloro-5-((4-((6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methyl)-1H-indole-2-carbonitrile hydrochloride [ No CAS ]
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  • 1-((1H-pyrazol-4-yl)methyl)-6-hydroxy-5-((4-((6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methyl)-1H-indole-2-carbonitrile hydrochloride [ No CAS ]
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  • 1-((1H-pyrazol-4-yl)methyl)-6-methoxy-5-((4-((6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methyl)-1H-indole-2-carbonitrile hydrochloride [ No CAS ]
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  • 4-chloro-5-methyl-1H-indole-2-carbonitrile [ No CAS ]
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  • [ 61563-28-8 ]
  • 4-chloro-5-formyl-1H-indole-2-carbonitrile [ No CAS ]
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  • 4-chloro-5-((4-((6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methyl)-1H-indole-2-carbonitrile [ No CAS ]
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  • 5-formyl-6-methoxy-1H-indole-2-carbonitrile [ No CAS ]
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  • 5-formyl-6-methoxy-1-((1-trityl-1H-pyrazol-4-yl)methyl)-1H-indole-2-carbonitrile [ No CAS ]
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  • 1-((1H-pyrazol-4-yl)methyl)-6-methoxy-5-((4-((6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methyl)-1H-indole-2-carbonitrile [ No CAS ]
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  • [ 61563-28-8 ]
  • 1-((1H-pyrazol-4-yl)methyl)-6-hydroxy-5-((4-((6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methyl)-1H-indole-2-carbonitrile [ No CAS ]
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  • (Z)-methyl 2-azido-3-(2-chloro-3-methylphenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; at -20 - 25℃; for 14h; To a solution of MeONa (17.2 g, 319 mmol) in methanol (150 mL) was added a solution of methyl 2-azidoacetate (41.2 g, 319 mmol) and 2-chloro-3-methyl-benzaldehyde (16.4 g, 106 mmol) in methanol (150 mL) dropwise at -20 C. After the mixture was stirred at -20 C for 2 hrs, it was warmed up to 25 C for 12 hrs. During this time a fine precipitate was formed. The suspension was poured onto ice water and the azido derivative was collected by filtration and the filter cake washed with cold water. The solid was dissolved in dichloromethane (200 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel chromatography (petroleum ether:ethyl acetate = 10:1) to give the title compound. 1H NMR (400MHz, CDCl3) delta = 8.04 - 7.95 (m, 1H), 7.37 (s, 1H), 7.26 - 7.20 (m, 2H), 3.96 (s, 3H), 2.48 - 2.37 (m, 3H).
With methanol; sodium methylate; at -20 - 25℃; for 14h; Step 3 - (Z)-Methyl 2-azido-3-(2-chloro-3-methylphenyl)acrylate (0339) [00251] To a solution of MeONa (17.2 g, 319 mmol) in methanol (150 mL) was added a solution of methyl 2-azidoacetate (41.2 g, 319 mmol) and 2-chloro-3-methyl-benzaldehyde (16.4 g, 106 mmol) in methanol (150 mL) dropwise at -20 C. After the mixture was stirred at -20 C for 2 hrs, it was warmed up to 25 C for 12 hrs. During this time a fine precipitate was formed. The suspension was poured onto ice water and the azido derivative was collected by filtration and washed with cold water. The solid was dissolved in dichloromethane (200 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel chromatography (petroleum ether:ethyl acetate = 10:1) to give the title compound. 1H NMR (400MHz, CDCl3) delta = 8.04 - 7.95 (m, 1H), 7.37 (s, 1H), 7.26 - 7.20 (m, 2H), 3.96 (s, 3H), 2.48 - 2.37 (m, 3H).
  • 27
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  • (±)-tert-butyl 3-(4-chloro-1,5-dimethyl-1H-indole-2-carboxamido)-3-(4-(methylamino)-4-oxobutyl)piperidine-1-carboxylate [ No CAS ]
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  • [ 61563-28-8 ]
  • (±)-4-chloro-1.5-dimethyl-N-(3-(4-(methylamino)-4-oxobutyl)piperidin-3-yl)-1H-indole-2-carboxamide [ No CAS ]
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  • [ 61563-28-8 ]
  • (±)-tert-butyl ((3-(4-chloro-1.5-dimethyl-1H-indole-2-carboxamido)-3-(4-(methylamino)-4-oxobutyl)piperidin-1-yl)sulfonyl)carbamate [ No CAS ]
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  • (±)-4-chloro-1,5-dimethyl-N-(3-(4-(methylamino)-4-oxobutyl)-1-(N-(methylcarbamoyl)sulfamoyl)piperidin-3-yl)-1H-indole-2-carboxamide [ No CAS ]
  • 31
  • [ 61563-28-8 ]
  • (±)-tert-butyl 3-(2-acetamidoethyl)-3-(4-chloro-1,5-dimethyl-1H-indole-2-carboxamido) piperidine-1-carboxylate [ No CAS ]
  • 32
  • [ 61563-28-8 ]
  • (±)-N-(3-(2-acetamidoethyl)piperidin-3-yl)-4-chloro-1.5-dimethyl-1H-indole-2-carboxamide [ No CAS ]
  • 33
  • [ 61563-28-8 ]
  • (±)-tert-butyl (3-(2-acetamidoethyl)-3-(4-chloro-1.5-dimethyl-1H-indole-2-carboxamido)piperidin-1-yl)sulfonylcarbamate [ No CAS ]
  • 34
  • [ 61563-28-8 ]
  • (±)-N-(3-(2-acetamidoethyl)-1-(N-(methylcarbamoyl)sulfamoyl)piperidin-3-yl)-4-chloro-1.5-dimethyl-1H-indole-2-carboxamide [ No CAS ]
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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