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Hydrochloric Acid → (6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amine

HRID 445539
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 445539
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2Cl.[NH2:16][C:17]1[C:18]([CH3:23])=[N:19][N:20]([CH3:22])[CH:21]=1.Cl.CN1C(C)(C)CCCC1(C)C>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[NH:16][C:17]1[C:18]([CH3:23])=[N:19][N:20]([CH3:22])[CH:21]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6603PempidineHCID 44310561,3-dimethyl-1H-pyrazol-4-amineHCID 219841286-Bromo-4-chloro-3-nitroquinoline

Produkt 1

HCID 59619997(6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374
Dimethylacetamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of 6-bromo-4-chloro-3-nitro-quinoline (Stage A.4, 3.0 g, 20.43 mmol) and 4-amino-1,3-dimethylpyrazole.HCl (ChemCollect, Remscheid, Germany, 1.85 g, 12.53 mmol) in DMA (45 ml) was added 1,2,2,6,6-pentamethylpiperidine (6.67 ml, 36.5 mmol). The RM was stirred at 50° C. for 4.5 h. Then the RM was cooled down to rt and quenched with H2O. The suspension was filtered, the solid cake was washed with H2O and dried under vacuum, before being dissolved in EtOAc. The solution was washed with brine (2×), dried over Na2SO4, filtered and evaporated to dryness to give the title compound as an orange solid (HPLC tR 2.55 min (Method A); M+H=362; M−H=360 MS-ES)

Aufarbeitung

  1. temperatureThen the RM was cooled down to rt
  2. customquenched with H2O
  3. filtrationThe suspension was filtered
  4. washthe solid cake was washed with H2O
  5. customdried under vacuum
  6. dissolutionbefore being dissolved in EtOAc
  7. washThe solution was washed with brine (2×)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-107e0d394ec241819ab4fdd628a3d338
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08476294B2

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