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Hydrochloric Acid → N-[3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-propyl]hydroxyl-amine

HRID 1761572
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1761572
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][CH:23]=[N:24][OH:25])[CH:9]=2)=[CH:4][CH:3]=1.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.[BH3-]C#N.[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21][CH2:22][CH2:23][NH:24][OH:25])[CH:9]=2)=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 54403492HCID 54403492, Verbindung

Produkt 1

HCID 14497546N-[3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-propyl]hydroxyl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of the oxime 26 (2.70 g, 7.59 mM) in MeOH (50 ml), containing methyl orange (2 mg) as as indicator, was added a solution of NaBH3CN (0.52 g, 8.4 mM) in MeOH (20 ml), and a solution of 2N HCl, simultaneously, at such a rate to maintain a pH of 3 to 4. The reaction was stirred for 3 hours at room temperature, acidified to pH 1 and concentrated in vacuo. The residue was diluted with H2O (100 ml), adjusted to pH 8.5 with 5N NaOH, and extracted with EtOAc. The extracts were combined, dried (Na2SO4), filtered and concentrated in vacuo. The residue was chromatographed on Merck Silica Gel 60 (90 g, 230-400 mesh) with EtOAc:MeOH (9:1) as eluent. Crystallization from Et2O afforded pure 38 (1.64 g, 60%) as a white solid, mp=91°-93°. MS, m/e 357(M+).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with H2O (100 ml)
  3. extractionextracted with EtOAc
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on Merck Silica Gel 60 (90 g, 230-400 mesh) with EtOAc:MeOH (9:1) as eluent
  8. customCrystallization from Et2O afforded pure 38 (1.64 g, 60%) as a white solid, mp=91°-93°

Quellen und Nachweise

ORD-Eintrag
ord-f724477a705d4aa7a36fab78976fd40d
Quelldatensatz
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04826868

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