Phosphorus oxychloride → 3-Chloro-2-(4-chloro-2-fluoro-5-propan-2-yloxyphenyl)-4,5,6,7-tetrahydroindazole

HRID 1762986Notes

Reaction equation

HRID 1762986 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][C:5]([N:12]2[C:20](=O)[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=3[NH:13]2)=[C:4]([F:22])[CH:3]=1.P(Cl)(Cl)([Cl:25])=O>C(Cl)(Cl)Cl>[Cl:25][C:20]1[N:12]([C:5]2[CH:6]=[C:7]([O:8][CH:9]([CH3:11])[CH3:10])[C:2]([Cl:1])=[CH:3][C:4]=2[F:22])[N:13]=[C:14]2[C:19]=1[CH2:18][CH2:17][CH2:16][CH2:15]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15588633HCID 15588633, compound

Product 1

HCID 1850793-Chloro-2-(4-chloro-2-fluoro-5-propan-2-yloxyphenyl)-4,5,6,7-tetrahydroindazoleYield 28.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-one (1 g) and phosphorus oxychloride (0.7 g) was heated under reflux heating for 6 hours. After cooling, the reaction mixture was dissolved in chloroform, washed with a 5% sodium hydroxide solution and water, dried and concentrated. The residue was purified by silica gel column chromatography to give 0.3 g of 3-chloro-2-(4-chloro-2-fluoro-5-isopropoxyphenyl)-4,5,6,7-tetrahydro-2H-indazole (Compound No. 2). nD26 1.5530.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureheating for 6 hours
  4. temperatureAfter cooling
  5. washwashed with a 5% sodium hydroxide solution and water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-66590d7bab9e44c7888569c6795af143
Source dataset
uspto-grants-1989_05
Patent number
US04835286

Reaction notes

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