Chlorobenzene → 1H-Indazole

HRID 1352111Notes

Reaction equation

HRID 1352111 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5](O)=[CH:6][CH:7]=1.ClC1C=CC=CC=1.C([O-])(=O)C.[K+].[N+:22]([O-])(OCCC(C)C)=O>C(OC(=O)C)(=O)C>[NH:1]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=[N:22]1

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 10985Isoamyl nitrateHCID 178194-Amino-m-cresolHCID 517044Potassium Acetate

Product 1

HCID 92211H-Indazole

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

4-Amino-m-cresol is suspended in acetic anhydride and chlorobenzene in the presence of potassium acetate, isoamyl nitrate is added to the suspension at 70° C. to 100° C., preferably about 80° C., and the mixture is stirred to form an indazole skeleton. The intermediate thus obtained is dissolved in hydrochloric acid-methanol, and the mixture is preferably stirred at room temperature to deacetylate the compound.

Sources & evidence

ORD record
ord-ab633d2329714fbf88ae9b8d8b6425e7
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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