6-Nitroindazole → HCID 178526457, compound

HRID 388934

Reaction equation

HRID 388934 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:16])(=O)=O>ClCCCl>[Cl:16][C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:10][N:9]=1

Participants

4

Reactant 2

HCID 242396-NitroindazoleHCID 24648Sulfuryl chloride

Product 1

HCID 178526457HCID 178526457, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-nitroindazole (2 mmol) in DCE (5 mL), sulfuryl chloride (10 mmol) was added and the resulting mixture was heated 80° C. for 3-5 h. The reaction mixture was concentrated, added with 5% aqueous Na2CO3 solution (20 mL) and extracted with EtOAc (2×15 mL). The combined organics were then washed with water (20 mL) and brine (20 mL) and dried over anhydrous Na2SO4. Removal of volatiles afforded 3-chloro-6-nitro-1H-indazole as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionadded with 5% aqueous Na2CO3 solution (20 mL)
  3. extractionextracted with EtOAc (2×15 mL)
  4. washThe combined organics were then washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customRemoval of volatiles

Sources & evidence

ORD record
ord-62054ca5d7a94f238984c26777a25bb4
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Linked notes

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