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Chemical Structure| 37033-95-7

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Product Details of [ 37033-95-7 ]

CAS No. :37033-95-7
Formula : C18H17NO3
M.W : 295.33
SMILES Code : O=C(C(N1)=CC2=C1C=CC(OCC3=CC=CC=C3)=C2)OCC
MDL No. :MFCD00022702
InChI Key :DCIFXYFKVKDOLL-UHFFFAOYSA-N
Pubchem ID :95721

Safety of [ 37033-95-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 37033-95-7 ]

* 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 [ 37033-95-7 ]

[ 37033-95-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 37033-95-7 ]
  • [ 24985-85-1 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen;10% palladium on activated carbon; In ethanol; for 20h; A solution of 5-benzyloxyindole-2-carboxylic acid ethyl ester (10 g, 34 mmol) in ethanol (250 mL) was treated with 10% Pd/C and hydrogenated under atmospheric pressure (double-walled balloon) for 20 h. The reaction mixture was diluted with EtOAc and filtered through Celite. Evaporation of the filtrate in vacuo gave the title compound as a tan solid (7 g, 99%). 1H NMR (400 MHz, CDCl3) delta 8.86 (br s, 1H), 7.29 (d, J=8.80 Hz, 1H), 7.11 (s, 1H), 7.06 (s, 1H), 6.94 (d, J=8.70 Hz, 1H), 4.83 (br s, 1H), 4.42 (q, J=7.09 Hz, 2H), 1.41 (t, J=7.08 Hz, 3H).
99% palladium-carbon; In ethanol; a Ethyl 5-Hydroxyindole-2-carboxylate A solution of 5-benzyloxyindole-2-carboxylic acid ethyl ester (10 g, 34 mmol) in 250 mL of ethanol was treated with 10% Pd/C and hydrogenated under atmospheric pressure (double-walled balloon) for 20 h. The reaction mixture was diluted with EtOAc and filtered through Celite. Evaporation of the filtrate in vacuo gave the title compound as a tan solid (7 g, 99%). 1H NMR (400 MHz, CDCl3) delta 8.86 (br s, 1H), 7.29 (d, J=8.80 Hz, 1H), 7.11 (s, 1H), 7.06 (s, 1H), 6.94 (d, J=8.70 Hz, 1H), 4.83 (br s, 1H), 4.42 (q, J=7.09 Hz, 2H), 1.41 (t, J =7.08 Hz, 3H).
99% palladium-carbon; In ethanol; a 5-Hydroxyindole-2-carboxylic Acid Ethyl Ester A solution of 5-benzyloxyindole-2-carboxylic acid ethyl ester (10 g, 34 mmol) in ethanol (250 mL) was treated with 10% Pd/C and hydrogenated under atmospheric pressure (double-walled balloon) for 20 h. The reaction mixture was diluted with EtOAc and filtered through Celite. Evaporation of the filtrate in vacuo gave the title compound as a tan solid (7 g, 99%). 1H NMR (400 MHz, CDCl3)·8.86 (br s, 1H), 7.29 (d, J=8.80 Hz, 1H), 7.11 (s, 1H), 7.06 (s, 1H), 6.94 (d, J=8.70 Hz, 1H), 4.83 (br s, 1H), 4.42 (q, J=7.09 Hz, 2H), 1.41 (t, J=7.08 Hz 3H).
  • 2
  • [ 926-06-7 ]
  • [ 37033-95-7 ]
  • [ 938081-51-7 ]
YieldReaction ConditionsOperation in experiment
90% With caesium carbonate; In acetonitrile; for 18h;Heating / reflux; To a mixture of 5-benzyloxyindole-2-carboxylic acid ethyl ester (30 g, 1.0 eq.) and cesium carbonate (58. g, 1.75 eq.) in acetonitrile (200 mL), was added isopropylmethane sulfonate (24.8 g, 1.75 eq.). The reaction mixture was refluxed for 18 h and then concentrated in vacuo. The residue was partitioned between water and methyl-tert-butylether. The aqueous layer was extracted with methyl-tert-butylether and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and dried in vacuo. then purified on silica eluding with dichloromethane/methanol 98:2 v:v. The crude material was purified by crystallization in ethanol and dried in vacuo to yield 31 g (90percent) of the desired product as an off-white oil. MS (m/e): 338.4 (MH+, 100percent).
 

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