Methane → 6-Oxo-1(6H)-pyridazinepropanenitrile

HRID 1733552Notes

Reaction equation

HRID 1733552 reaction equation
[N:1]1[NH:2][C:3](=[O:7])[CH:4]=[CH:5][CH:6]=1.[C:8](#[N:11])[CH:9]=[CH2:10].[OH-].C[N+](C)(C)CC1C=CC=CC=1.C>C(O)C.CO>[O:7]=[C:3]1[CH:4]=[CH:5][CH:6]=[N:1][N:2]1[CH2:10][CH2:9][C:8]#[N:11]

Participants

7

Reactant 4

HCID 297MethaneHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 681533(2H)-Pyridazinone

Product 1

HCID 5660246-Oxo-1(6H)-pyridazinepropanenitrileYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3.84 g (0.04 mole) of 3(2H)-pyridazinone, 2.33 g (0.044 mole) of acrylonitrile in 50 ml of ethanol, 1 ml of Triton-B (trimethyl benzylammonium hydroxide, 40% methanol solution) was added dropwise. The mixture was stirred for 2 hours at 60° C. and then evaporated to dryness in a vacuum on a steam bath, giving a dark orange oil. The oil was dissolved in ethanol, shaken with Norit and filtered. The filtrate was distilled. Recrystallization of the residue from ethanol and isopropyl ether gave 4.7 g (79% yield) of 3-(3-oxo-2-pyridazinyl)-propionitrile in the form of pale yellow crystals, m.p. 75°-76° C.

Workup

  1. customevaporated to dryness in a vacuum on a steam bath
  2. customgiving a dark orange oil
  3. filtrationfiltered
  4. distillationThe filtrate was distilled
  5. customRecrystallization of the residue from ethanol and isopropyl ether

Sources & evidence

ORD record
ord-6446c35dabff4fa5b51e83ae6f846ec7
Source dataset
uspto-grants-1980_12
Patent number
US04242512

Reaction notes

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