Hydrochloric Acid → HCID 10946495, compound

HRID 2289843Notes

Reaction equation

HRID 2289843 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[CH:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])=[CH:4][CH:3]=1.[C:17]([CH2:19][C:20](OCC)=[O:21])#[N:18].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20](=[O:21])[C:19]([C:17]#[N:18])=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 691428133,3,3-Trifluoro-2-oxopropanal 1-(4-chlorophenylhydrazone)

Product 1

HCID 10946495HCID 10946495, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
110 °C

Procedure

After 0.281 g of 3, 3, 3-trifluoro-2-oxopropanal 1-(4-chlorophenylhydrazone) was dissolved in 5 mL of pyridine, 0.304 g of ethyl cyanoacetate was added to the pyridine solution, which was followed by stirring for 5 hours at 110° C. After cooling to room temperature, the reaction mixture was poured into 3N-hydrochloric acid and extracted with diethyl ether. After the organic layer was washed with aqueous saturated sodium bicarbonate and concentrated, the residue was subjected to silica gel column chromatography (eluent: ethyl acetate/hexane =1/9), and furthermore recrystallized from a solvent mixture (toluene/hexane =1/3) to afford 0.234 g of 2-(4-chlorophenyl)-4-cyano-5-trifluoromethylpyridazin-3-one (The present compound 1-15). 1H-NMR (300 MHz, CDCl3)δ(ppm): 7.49(2H, d, J=8.8 Hz), 7.61 (2H, d, J=8.8 Hz), 8.19 (1H,s)

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with diethyl ether
  3. washAfter the organic layer was washed with aqueous saturated sodium bicarbonate
  4. concentrationconcentrated
  5. customfurthermore recrystallized from a solvent mixture (toluene/hexane =1/3)

Sources & evidence

ORD record
ord-34cdc58cfda5464285fc10b7f5c703f9
Source dataset
uspto-grants-2000_07
Patent number
US06093818

Reaction notes

Loading…