alpha-Hydrazino-m-cresol dihydrochloride → 6-(3,5-Dibromo-4-hydroxyphenyl)-2-(3-hydroxybenzyl)-4,5-dihydropyridazin-3(2H)-one

HRID 2061415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061415
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH2:11][CH2:12][C:13]([OH:15])=O)[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].Cl.Cl.[OH:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[CH2:23][NH:24][NH2:25]>C(O)C>[Br:9][C:6]1[CH:5]=[C:4]([C:10]2[CH2:11][CH2:12][C:13](=[O:15])[N:24]([CH2:23][C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([OH:19])[CH:21]=3)[N:25]=2)[CH:3]=[C:2]([Br:1])[C:7]=1[OH:8]

Komponenten

4

Edukt 2

HCID 2724402alpha-Hydrazino-m-cresol dihydrochlorideHCID 45806384-(3,5-Dibromo-4-hydroxyphenyl)-4-oxobutanoic acid

Produkt 1

HCID 1361599086-(3,5-Dibromo-4-hydroxyphenyl)-2-(3-hydroxybenzyl)-4,5-dihydropyridazin-3(2H)-oneAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobutanoic acid (H) (150 mg, 0.426 mmol) and 3-hydroxybenzylhydrazine dihydrochloride (135 mg, 0.639 mmol) in ethanol was heated to reflux. After heating for 16 h, the reaction mixture was cooled down and the precipitate formed was collected and dried in vacuo. This gave the title compound as a red solid (95 mg, 49%)1H NMR δ (ppm) (DMSO-d6): 2.59 (2 H, t), 3.01 (2 H, t, J=8.2 Hz), 4.88 (2H, s), 6.67 (1 H, d, J=8.2 Hz), 6.69-6.76 (2 H, m), 7.14 (1 H, t, J=7.8 Hz), 7.92 (2 H, s), 9.39 (1 H, s), 10.44 (1 H, s). LCMS (10 cm_apci_formic) Rt 3.33 min; m/z 453/455/457 [M+H].

Aufarbeitung

  1. temperaturewas heated to reflux
  2. temperatureAfter heating for 16 h
  3. temperaturethe reaction mixture was cooled down
  4. customthe precipitate formed
  5. customwas collected
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4df88f1c7e604e81a5f35556b16e5c94
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283351B2

Notizen zur Reaktion

Wird geladen…