Thionyl Chloride → HCID 68552629, compound

HRID 1897623Notes

Reaction equation

HRID 1897623 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]([OH:17])=O>C1(C)C=CC=CC=1>[CH3:5][C:6]1[CH:14]=[CH:13][C:12]2=[N:11][N:10]3[C:9]([C:15](=[O:17])[N:10]4[N:11]=[C:12]5[C:8]([CH:7]=[C:6]([CH3:5])[CH:14]=[CH:13]5)=[C:9]4[C:15]3=[O:17])=[C:8]2[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1927385-Methylindazole-3-carboxylic acid

Product 1

HCID 68552629HCID 68552629, compoundYield 135.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (11 ml; 0.151 mol) was added to a suspension of 5-methyl-1H-indazole-3-carboxylic acid (12.2 g; 0.056 mol), prepared as described in J. Heterocyclic Chem. 1964, Vol. 1 (5) 239-241, in toluene (130 ml), and the reaction mixture was refluxed for 4 hours. The solvent was removed by evaporation under reduced pressure and the residue was taken up twice in toluene to give 12 g of the desired product.

Workup

  1. customprepared
  2. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-23da64c428534939bf1c30f1f149415f
Source dataset
uspto-grants-2013_08
Patent number
US08519139B2

Reaction notes

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