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Chemical Structure| 58518-51-7 Chemical Structure| 58518-51-7

Structure of 58518-51-7

Chemical Structure| 58518-51-7

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Product Details of [ 58518-51-7 ]

CAS No. :58518-51-7
Formula : C10H9NO
M.W : 159.18
SMILES Code : O=CC(N1)=CC2=C1C=CC=C2C
MDL No. :MFCD13185706
InChI Key :CGUYNKDWQDSGJU-UHFFFAOYSA-N
Pubchem ID :18006462

Safety of [ 58518-51-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P264-P280-P305+P351+P338-P337+P313

Application In Synthesis of [ 58518-51-7 ]

* 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 [ 58518-51-7 ]

[ 58518-51-7 ] Synthesis Path-Downstream   1~1

  • 1
  • 4-methylindole-2-carboxylic acid-(N'-tosyl-hydrazide) [ No CAS ]
  • 2-methylbenzenesulphochloride [ No CAS ]
  • [ 16732-80-2 ]
  • [ 20948-63-4 ]
  • [ 58518-51-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; hydrazine hydrate; In pyridine; ethylene glycol; toluene; EXAMPLE 1 -- Preparation of 4-methylindole-2-carbaldehyde 25 g 4-methylindole-2-carboxylic acid ethyl ester (C.A. 52, 6314(a)) and 50 ml hydrazine hydrate were heated for six hours while stirring and under reflux at 120 C. bath temperature. After cooling, the crystallized 4-methylindole-2-carboxylic acid hydrazide was filtered off with suction and washed thoroughly with ethanol. Yield 23.0 g (= 98.5% of theory); melting point 269-273 C. 23.0 g 4-methylindole-2-carboxylic acid hydrazide were added in small portions, while stirring and during ice cooling, to the solution of 23.0 g p-toluene sulfochloride in 300 ml pyridine. Then it was stirred for another hour in the ice bath and for another hour at room temperature, poured onto a mixture of 350 ml concentrated hydrochloric acid and ice, the precipitated 4-methylindole-2-carboxylic acid-(N'-tosyl-hydrazide) filtered off with suction and thoroughly washed with well diluted hydrochloric acid, then with water. Yield: 38.3 g(= 92% theory); (melting point) 242-245 C. (decomposition). 38.0 g 4-methylindole-2-carboxylic acid-(N'-tosyl hydrazide) were added to the suspension preheated to 160 C. of 38 g anhydrous soda in 380 ml ethylene glycol. The reaction took place with vigorous foaming. As soon as this stopped, the mixture was poured onto ice, the substance filtered off with suction, dissolved in toluene, the solution dried, carbonized and substantially concentrated. The 4-methylindole-2-carbaldehyde (crude yield about 43% of theory) was recrystallized twice from toluene. Yield: 4.2 g (= 23.8% of theory); melting point 147-149 C.
 

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