Benzene → HCID 19081402, compound

HRID 963196Notes

Reaction equation

HRID 963196 reaction equation
C1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[N:12][N:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:10](=[O:18])[C:9]=1[OH:19].C(=O)[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>[C:14]([N:11]1[C:10](=[O:18])[CH:9]([OH:19])[C:8](=[N:7][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH:13]=[N:12]1)([CH3:16])([CH3:15])[CH3:17]

Participants

6

Reactant 3

HCID 241BenzeneHCID 133894-PyridinecarboxaldehydeHCID 178448755HCID 178448755, compound

Product 1

HCID 19081402HCID 19081402, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

50 ml of a dry benzene solution of 3.1 g of 5-amino-2-tert-butyl-4-hydroxypyridazin-3-(2H)-one, 1.9 g of isonicotinaldehyde and 0.17 g of p-toluene sulfonic acid, was reacted for 1.5 hours under heating and refluxing by means of a Dean Stark trap. After cooling, 100 ml of ethyl acetate was added to the reaction mixture, and the mixture was washed with water and then with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 3.3 g of 2-tert-butyl-4-hydroxy-5-(4-pyridylimino)pyridazin-3-(2H)-one as a powder.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing by means of a Dean Stark trap
  3. temperatureAfter cooling
  4. washthe mixture was washed with water
  5. dry with materialwith a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c4567f0329c34b74bbfb70c81ded8744
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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