Water → 2h-Indazole, 3-chloro-2-(2,4-dichloro-5-(difluoromethoxy)phenyl)-4,5,6,7-tetrahydro-

HRID 2309313Notes

Reaction equation

HRID 2309313 reaction equation
[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[C:15]([OH:17])[C:14]([Cl:18])=[CH:13][C:12]=2[Cl:19])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2.O.[OH-].[Na+].Cl[CH:24]([F:26])[F:25]>O1CCOCC1>[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[C:15]([O:17][CH:24]([F:26])[F:25])[C:14]([Cl:18])=[CH:13][C:12]=2[Cl:19])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 6372ChlorodifluoromethaneHCID 14798Sodium Hydroxide2×HCID 1847652,4-Dichloro-5-(3-chloro-4,5,6,7-tetrahydroindazol-2-yl)phenol

Product 1

HCID 1847632h-Indazole, 3-chloro-2-(2,4-dichloro-5-(difluoromethoxy)phenyl)-4,5,6,7-tetrahydro-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6.4 g of 3-chloro-2-(2,4-dichloro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole II-1 in 12.5 ml of dioxane were added 12.5 ml of water and 6.4 g of 50% sodium hydroxide. The mixture was heated at 50°~60° C., mixed with excessive amount of chlorodifluoromethane, and heated at 50°~60° C. To the mixture was dropwise added 6.4 g of 50% sodium hydroxide respectively 2.5 hours later and 4 hours later within 15 minutes. The resulting mixture was allowed to react for 2.5 hours, cooled, neutralized, and extracted with ether. The extract was washed with saturated aqueous sodium chloride, dried and concentrated. The residue was purified by silica-gel chromatography to give 4.0 g of the titled compound I-1.

Workup

  1. temperatureThe mixture was heated at 50°~60° C.
  2. temperatureheated at 50°~60° C
  3. customto react for 2.5 hours
  4. temperaturecooled
  5. extractionextracted with ether
  6. washThe extract was washed with saturated aqueous sodium chloride
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-ade6d47c9394451aae912213c426c413
Source dataset
uspto-grants-1987_09
Patent number
US04695312

Reaction notes

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