Hydrazine hydrate (1:1) → 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol

HRID 1712954

Reaktionsgleichung

Reaktionsgleichung von HRID 1712954
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=O.O.[NH2:19][NH2:20]>C(O)C>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:10]2[CH2:9][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[NH:20][N:19]=2)[CH:13]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 5387155(2E)-3-(2-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one

Produkt 1

HCID 226963962-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of (2E)-3-(2-hydroxyphenyl)-1-pyridin-3-ylprop-2-en-1-one (12.5 g, 55.6 mmol), hydrazine monohydrate (6.00 mL, 123 mmol), and ethanol (160 mL) was allowed to stir at 80° C. overnight. The reaction mixture was filtered over a pad of celite and washed with MeOH and DCM. The resulting filtrate was concentrated to give 2-(3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (12.5 g, 94%) as a light grey solid. 1H NMR (400 MHz, d6-DMSO, HCl salt) δ: 9.52-9.67 (bs, 1H), 8.78 (s, 1H), 8.45-8.51 (m, 1H), 7.97 (d, 1H), 7.61 (s, 1H), 7.38 (t, 1H), 7.26 (d, 1H), 7.07 (t, 1H), 6.81 (d, 1H), 6.76 (t, 1H), 5.04 (t, 1H), 3.44 (dd, 1H), and 2.76 (dd, 1H). LCMS: (FA) ES+ 240.2, ES-238.5.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over a pad of celite
  2. washwashed with MeOH and DCM
  3. concentrationThe resulting filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-68997e3cde8f497280d2dbee31ddd9dd
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795249B2

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