Phosphorus oxychloride → 2H-Indazole, 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-

HRID 1439340Notes

Reaction equation

HRID 1439340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=O)[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[NH:9]2)=[C:4]([F:18])[CH:3]=1.P(Cl)(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][C:16]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:18])[N:9]=[C:10]2[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 227482812-(4-Chloro-2-fluorophenyl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-one

Product 1

HCID 946072H-Indazole, 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10.0 Parts of 2-(4-chloro-2-fluorophenyl)-1,2,4,5,6,7 -hexahydro-3H-indazol-3-one and 7.3 parts of phosphorous oxychloride were mixed and heated to 130°-150° for six hours. The reaction mixture was dissolved in 100 parts of chloroform. The organic solution containing the product was washed successively with three portions of 25 parts each of 10% sodium hydroxide and then washed with 50 parts water. The chloroform solution was dried with 2-10 parts of anhydrous sodium sulfate and then filtered. The solvent was removed under a reduced pressure on a rotary evaporator. The resulting thick oil was purified by sublimation at 100°-120° at 0.5-1.5 mm. pressure to yield 7.8 parts of white crystalline material with m.p. 88°-89.5°.

Workup

  1. temperatureheated to 130°-150° for six hours
  2. additionThe organic solution containing the product
  3. washwas washed successively with three portions of 25 parts each of 10% sodium hydroxide
  4. washwashed with 50 parts water
  5. dry with materialThe chloroform solution was dried with 2-10 parts of anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under a reduced pressure on a rotary evaporator
  8. customThe resulting thick oil was purified by sublimation at 100°-120° at 0.5-1.5 mm
  9. custompressure to yield 7.8 parts of white crystalline material with m.p. 88°-89.5°

Sources & evidence

ORD record
ord-69b157b7058649a0b11d5def5b462626
Source dataset
uspto-grants-1977_11
Patent number
US04059434

Reaction notes

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