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Pyridine → HCID 11463284, Verbindung

HRID 1357237
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1357237
[C:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH3:14])=[C:10]([C:15](Cl)=[O:16])[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:18][CH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH:26]=[C:25]([OH:30])[CH:24]=[CH:23]2.N1C=CC=CC=1>C(Cl)Cl>[OH:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([CH2:19][NH:18][C:15]([C:10]1[CH:9]=[N:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]=1[CH2:12][CH2:13][CH3:14])=[O:16])[CH:29]=[CH:28]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 37757171-Phenyl-5-propyl-1H-pyrazole-4-carbonyl chlorideHCID 118161426-(Aminomethyl)-2-naphthol

Produkt 1

HCID 11463284HCID 11463284, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-phenyl-5-propyl-1H-pyrazole-4-carbonyl chloride (2.0 g, 8 mmol) in 20 mL of methylene chloride was added dropwise under nitrogen to a mixture of 6-aminomethyl-naphthalen-2-ol (1.63 g, 9.42 mmol), prepared in step 1 of Example 8, and 75 mL of anhydrous pyridine. The reaction stirred at room temperature for 17 h (overnight). The reaction was diluted with methylene chloride and extracted with 1N HCl. The aqueous layer was separated and extracted with methylene chloride. The organic extracts were combined, dried (MgSO4) and the solvent removed under reduced pressure to give a brown solid. The solid was recrystallized from ethyl acetate and then again from isopropanol. The crystals were collected by filtration and dried under reduced pressure to give 1-phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide (0.767 g, 25%) as a tan solid, mp 189-190° C.

Aufarbeitung

  1. extractionextracted with 1N HCl
  2. customThe aqueous layer was separated
  3. extractionextracted with methylene chloride
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. customto give a brown solid
  7. customThe solid was recrystallized from ethyl acetate
  8. filtrationThe crystals were collected by filtration
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-805a7ba6f22c47da8bc8d530b9409f1f
Quelldatensatz
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06589970B2

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