2-Amino-5-chloropyridine → HCID 86654450, compound

HRID 552622Notes

Reaction equation

HRID 552622 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([C:17]2([C:32]([F:35])([F:34])[F:33])[O:21][N:20]=[C:19]([C:22]3[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[C:24]([CH3:31])[CH:23]=3)[CH2:18]2)[CH:13]=[C:14]([Cl:16])[CH:15]=1>N1C=CC=CC=1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([C:19]3[CH2:18][C:17]([C:12]4[CH:13]=[C:14]([Cl:16])[CH:15]=[C:10]([Cl:9])[CH:11]=4)([C:32]([F:35])([F:34])[F:33])[O:21][N:20]=3)=[CH:23][C:24]=2[CH3:31])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 86654450HCID 86654450, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a solution of 0.59 g of 2-amino-5-chloropyridine in 10 mL of pyridine, 2.0 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methylbenzoyl-chloride synthesized in Step 4 of Synthetic Example 1 was added at room temperature with stirring, and stirred at the same temperature for 15 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in 50 mL of ethyl acetate, then washed with 3N hydrochloric acid (50 mL×1), and then the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with neutral alumina column chromatography that was eluated with chloroform to obtain 1.80 g of the aimed product as white crystal.

Workup

  1. stirringstirred at the same temperature for 15 hours
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in 50 mL of ethyl acetate
  5. washwashed with 3N hydrochloric acid (50 mL×1)
  6. dry with materialdried over saturated sodium chloride aqueous solution
  7. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  8. customThe residue was purified with neutral alumina column chromatography that

Sources & evidence

ORD record
ord-200fca5c7c104db190dcca0e8a3d7926
Source dataset
uspto-grants-2011_05
Patent number
US07951828B1

Reaction notes

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