Dimethylformamide → methyl 6-oxo-3,4-diphenyl-1(6H)-pyridazinenonanoate

HRID 981474

Reaction equation

HRID 981474 reaction equation
CN(C=O)C.[C:6]1([C:12]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:16][NH:15][C:14](=[O:24])[CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35]>O>[O:24]=[C:14]1[N:15]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[N:16]=[C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:13]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1509765,6-Diphenyl-3(2H)-pyridazinoneHCID 554142Methyl 9-bromononanoate

Product 1

HCID 9931844methyl 6-oxo-3,4-diphenyl-1(6H)-pyridazinenonanoateYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (840 mg of a 60% dispersion in oil, 20 mmol) was washed twice with hexanes, covered with DMF (25 mL) and 5,6-diphenyl-3(2H)-pyridazinone (4 g, 16 mmol), obtained according to P. Schmidt, et al., Helvetica Chim. Acta., 37, 134-140 (1954), added. After gas evolution had ceased, the mixture was stirred at room temperature for 30 minutes before adding methyl 9-bromononanoate (4.45 g, 18 mmol). The mixture was heated briefly to 110° C. to give a solution and then allowed to cool before being stirred at room temperature for 1 hour. The mixture was diluted with water and extracted with diethyl ether (3×). The combined extracts were washed with water, dried over sodium sulfate and concentrated to leave an oil. Chromatography on a column of silica gel afforded methyl 6-oxo-3,4-diphenyl-1(6H)-pyridazine nonanoate (6.44 g, 95%) as an oil.

Workup

  1. washSodium hydride (840 mg of a 60% dispersion in oil, 20 mmol) was washed twice with hexanes
  2. customobtained
  3. addition, 37, 134-140 (1954), added
  4. temperatureThe mixture was heated briefly to 110° C.
  5. customto give a solution
  6. temperatureto cool
  7. stirringbefore being stirred at room temperature for 1 hour
  8. extractionextracted with diethyl ether (3×)
  9. washThe combined extracts were washed with water
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customto leave an oil

Sources & evidence

ORD record
ord-2de90a7cd6704c34a10f3605c9ea7f9c
Source dataset
uspto-grants-1991_02
Patent number
US04992439

Linked notes

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