Triethylamine → HCID 18676101, compound

HRID 1635484Notes

Reaction equation

HRID 1635484 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH2:9][C:10](=O)[CH3:11])[CH:5]=[CH:4][N:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.Cl.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:21]([C:18]3[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=3)[N:22]=[C:10]([CH3:11])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 18676105HCID 18676105, compound

Product 1

HCID 18676101HCID 18676101, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(2-chloro-4-pyridinyl)-1,3-butanedione (from step 2, Example 29) (2.5 g, 12.69 mmol), p-chlorophenylhydrazine·HCl (2.7 g, 15.11 mmol) and triethylamine (2.1 mL, 15.11 mmol) in ethanol (50 mL) was heated to reflux overnight (about eighteen hours). The resulting dark colored solution was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated to give 2-chloro-4-[1-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-yl]pyridine as an orange colored solid (1.5 g, 39%). MP: 110.05° C. This product was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight (about eighteen hours)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d3ee830d530643048d299e227eb426a5
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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