Ethanol → ethyl 1-(4-chloro-2-methylbenzyl)-1H-indazole-3-carboxylate

HRID 1256626

Reaktionsgleichung

Reaktionsgleichung von HRID 1256626
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([OH:18])=[O:17])=[N:8]2)=[C:4]([CH3:21])[CH:3]=1.OS(O)(=O)=O.[CH2:27](O)[CH3:28]>>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([O:18][CH2:27][CH3:28])=[O:17])=[N:8]2)=[C:4]([CH3:21])[CH:3]=1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 68679Tolnidamine

Produkt 1

HCID 67092644ethyl 1-(4-chloro-2-methylbenzyl)-1H-indazole-3-carboxylate

Versuchsvorschrift

To a suspension of 1-(4-chloro-2-methylbenzyl)-1H-indazole-3-carboxylic acid, prepared as described in J. Med. Chem. (1976) 19, 778-783, (120 g; 0.4 mol) in absolute ethanol (850 ml), stirred at room temperature, was cautiously added concentrated H2SO4 (15 ml). The mixture was then refluxed for 9 hours. The reaction was then completed by cooling the mixture to room temperature. The solid thus formed was filtered off under cold conditions (10° C.) and washed thoroughly on the filter with water. 126 g of ethyl 1-(4-chloro-2-methylbenzyl)-1H-indazole-3-carboxylate were thus obtained, and were used in the following reaction without further purification.

Aufarbeitung

  1. customprepared
  2. temperatureThe mixture was then refluxed for 9 hours
  3. customThe solid thus formed
  4. filtrationwas filtered off under cold conditions (10° C.)
  5. washwashed thoroughly on the
  6. filtrationfilter with water

Quellen und Nachweise

ORD-Eintrag
ord-687c3035028845ce82e372d09ce20f0b
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461194B2

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