Hydrochloric Acid → HCID 178419483, compound

HRID 1353648Notes

Reaction equation

HRID 1353648 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[Br:10]Br.Cl>[OH-].[Na+].S(=O)(O)[O-].[Na+]>[Br:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 92211H-IndazoleHCID 24408Bromine

Product 1

HCID 178419483HCID 178419483, compoundYield 107.4%

Reagents, catalysts & solvents 2

HCID 23665763Sodium BisulfiteCatalystHCID 14798Sodium HydroxideSolvent2×

Procedure

To a suspension of 1H-indazole (3.00 g, 25.4 mmol) in 2.0 M sodium hydroxide solution (70 mL) at ambient temperature was added a solution of bromine (3.00 g, 18.8 mmol) in 2.0 M sodium hydroxide solution (30 mL) dropwise. After stirring for 3 hours, to the reaction mixture was added sodium bisulfite (0.1 g), followed by 2.0 N hydrochloric acid solution (80 mL). The precipitates were filtered and washed with water to provide the title compound (3.98 g, 80% yield): mp 136° C.; 1N NMR (CDCl3) δ 13.4 (br s, 1H), 7.57 (m, 2H), 7.45 (t, 1H), 7.22 (t, 1H); EI-MS (m/z) 198 [M+2]+, 196 [M]+.

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-9d838ec1cb5d4578aaafb9d211560ae3
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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