Hydrogen Bromide → HCID 178515474, compound

HRID 1955587Notes

Reaction equation

HRID 1955587 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]C)=[CH:12][CH:13]=2)[C:8]([OH:17])=[N:7]1.Br.O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[C:8]([OH:17])=[N:7]1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 14798Sodium HydroxideHCID 178487266HCID 178487266, compound

Product 1

HCID 178515474HCID 178515474, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.85 g 1-(3,4-dichlorobenzyl)-5-methoxy-1H-indazole-3-ol are heated in 30 ml acetic acid and 30 ml 50% hydrobromic acid for 4 hours under gentle reflux. After cooling, the mixture is stirred into 250 ml water, rendered alkaline with concentrated sodium hydroxide solution and extracted twice with 80 ml tert-butyl methyl ether. The aqueous phase is acidified with sulfuric acid and extracted by shaking three times with 200 ml tert-butyl methyl ether. The combined ether phases are dried over sodium sulfate and distilled to dryness under vacuum. The residue is washed with a small amount of tert-butyl methyl ether and dried.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with 80 ml tert-butyl methyl ether
  3. extractionextracted
  4. dry with materialThe combined ether phases are dried over sodium sulfate
  5. distillationdistilled to dryness under vacuum
  6. washThe residue is washed with a small amount of tert-butyl methyl ether
  7. customdried

Sources & evidence

ORD record
ord-e0951522de2d4d14964791f7891de963
Source dataset
uspto-grants-1998_07
Patent number
US05776932

Reaction notes

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