4-Pyridazinecarbonitrile, 2,3-dihydro-3-oxo-5,6-diphenyl- → 2-(2'-Nitrobutyl)-4-cyano-5,6-diphenyl-3-(2H)-pyridazinone

HRID 463971Notes

Reaction equation

HRID 463971 reaction equation
[C:1]([C:3]1[C:4](=[O:21])[NH:5][N:6]=[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:2].C(O[CH2:26][CH:27]([N+:30]([O-:32])=[O:31])[CH2:28][CH3:29])(=O)C>N1C=CC=CC=1>[N+:30]([CH:27]([CH2:28][CH3:29])[CH2:26][N:5]1[C:4](=[O:21])[C:3]([C:1]#[N:2])=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:6]1)([O-:32])=[O:31]

Participants

4

Reactant 2

HCID 957574-Pyridazinecarbonitrile, 2,3-dihydro-3-oxo-5,6-diphenyl-HCID 2779722-Nitrobutyl acetate

Product 1

HCID 135335752-(2'-Nitrobutyl)-4-cyano-5,6-diphenyl-3-(2H)-pyridazinoneYield 38.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.0 grams (0.014 mole) of the product of Example 1 was reacted with 2.37 grams (0.014 mole) of 2-nitrobutyl acetate in 100 mls of dry pyridine. This solution was heated to reflux for 1 hour, cooled and the solvent distilled at reduced pressure. The residual solid was recrystallized from methyl alcohol to give 2.0 grams (37% yield) of a white-yellow solid melting at 154°-155° C. The infrared spectrum showed the C-C band at 3.5μ, the nitrile band at 4.5μ, and the amide carbonyl band at 6.0μ.

Workup

  1. temperatureThis solution was heated
  2. temperatureto reflux for 1 hour
  3. temperaturecooled
  4. distillationthe solvent distilled at reduced pressure
  5. customThe residual solid was recrystallized from methyl alcohol

Sources & evidence

ORD record
ord-2c26daaf842641a3aa5041bee81c18c4
Source dataset
uspto-grants-1985_10
Patent number
US04545810

Reaction notes

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