Ammonium Hydroxide → HCID 18676089, compound

HRID 1635518Notes

Reaction equation

HRID 1635518 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][N:14]=1)[CH2:5][C:6](=O)[CH2:7][C:8](=O)C.Cl.[F:16][C:17]1[CH:18]=[C:19]([NH:23][NH2:24])[CH:20]=[CH:21][CH:22]=1.[OH-].[NH4+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:23]([C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([F:16])[CH:18]=3)[N:24]=[C:7]([CH3:8])[CH:6]=2)[CH:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 27239143-Fluorophenylhydrazine hydrochlorideHCID 53955776HCID 53955776, compound

Product 1

HCID 18676089HCID 18676089, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-(2-chloroisonicotinyl)-1,3-butanedione (1.35 g, 0.068 mol) and 3-fluorophenylhydrazine hydrochloride (1.33 g, 0.0082 mol) in ethanol (40 mL) was added ammonium hydroxide (0.96 mL, 0.0082 mol) dropwise. The reaction mixture was heated at reflux overnight. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8) to give 1.54 g (79% yield) of product as a yellow oil: Anal. Calcd. for C15H11ClFN3: C, 62.62; H, 3.85; N, 14.60. Found: C, 62.34; H, 3.88; N, 14.30.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8)

Sources & evidence

ORD record
ord-06a671cadd9a4f67968a6b3a051a7a44
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

Loading…