Water → HCID 18699032, compound

HRID 2289844Notes

Reaction equation

HRID 2289844 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])=[C:4]([F:17])[CH:3]=1.[C:18]([CH2:20][C:21](OCC)=[O:22])#[N:19].N1CCCCC1.O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:21](=[O:22])[C:20]([C:18]#[N:19])=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[N:9]2)=[C:4]([F:17])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 70252960HCID 70252960, compound

Product 1

HCID 18699032HCID 18699032, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

After 1.0 g of 3, 3, 3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluorophenylhydrazone) was dissolved in 10 mL of pyridine, 0.8 mL of ethyl cyanoacetate and 0.5 mL of piperidine were added to the pyridine solution, which was followed by stirring for 3 days at room temperature. After pouring into water, the reaction solution was extracted with ethyl acetate. After the organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate and concentrated, the residue was subjected to silica gel column chromatography (eluent: ethyl acetate/hexane =4/1), and thin-layer chromatography (eluent: ethyl acetate/hexane =5/1) to afford 0.28g of 2-(4-chloro-2-fluorophenyl)-4-cyano-5-trifluoromethylpyridazin-3-one (The present compound 1-1).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washAfter the organic layer was washed with aqueous saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6209d34d9db5439ab0b7c4c01305e712
Source dataset
uspto-grants-2000_07
Patent number
US06093818

Reaction notes

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