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

HRID 2061415Notes

Reaction equation

HRID 2061415 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 1361599086-(3,5-Dibromo-4-hydroxyphenyl)-2-(3-hydroxybenzyl)-4,5-dihydropyridazin-3(2H)-oneYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-4df88f1c7e604e81a5f35556b16e5c94
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Reaction notes

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