Hydrochloric Acid → 1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine

HRID 1455614

Reaktionsgleichung

Reaktionsgleichung von HRID 1455614
Cl.[F:2][C:3]([F:17])([F:16])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][C:12]([NH2:15])=[N:11]2)[CH:7]=[CH:8][CH:9]=1.C(N(CC)CC)C.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.Cl>O1CCOCC1>[F:17][C:3]([F:2])([F:16])[C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[CH:13][C:12]([NH2:15])=[N:11]2)[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8471TriethylamineHCID 301874677992-29-1

Produkt 1

HCID 136269461-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(3-trifluoromethyl-phenyl)-4,5-dihydro-1H-pyrazol-3-ylamine hydrochloride salt (200 mg, 0.88 mmol) (Example 3A) in dioxane (50 mL) was added triethylamine (0.069 mL, 0.88 mmol) followed by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (200 mg, 0.88 mmol). The mixture was stirred at room temperature for 24 h and then poured onto dichloromethane. 2N hydrochloric acid was added and the organics extracted with 2N hydrochloric acid (3×50 mL). The acid layer was basified with 10N potassium hydroxide and extracted with dichloromethane (3×50 mL). The combined organics were dried (Na2SO4), filtered and evaporated to dryness. The residue dissolved in diethyl ether and 1M hydrochloric acid in diethyl ether was added to form a brown solid which was collected and dried (171 mg, 86%). MS (ES) m/z: 228.1 [M+H].

Aufarbeitung

  1. additionpoured onto dichloromethane
  2. extractionthe organics extracted with 2N hydrochloric acid (3×50 mL)
  3. extractionextracted with dichloromethane (3×50 mL)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. dissolutionThe residue dissolved in diethyl ether
  8. addition1M hydrochloric acid in diethyl ether was added
  9. customto form a brown solid which
  10. customwas collected
  11. customdried (171 mg, 86%)

Quellen und Nachweise

ORD-Eintrag
ord-cbf8e473c0364d45bc73ff649687c3b1
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482469B2

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