Water → HCID 19423537, compound

HRID 743073Notes

Reaction equation

HRID 743073 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl:23][C:24]([Cl:29])([Cl:28])[C:25](Cl)=[O:26].O>O1CCCC1>[C:8]([C:7]1[C:2]([NH:1][C:25](=[O:26])[C:24]([Cl:29])([Cl:28])[Cl:23])=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 12711129(2-Aminopyridin-3-yl)(phenyl)methanone

Product 1

HCID 19423537HCID 19423537, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 11.0 g (55 mmol) of 2-amino-3-benzoylpyridine and 6.1 g (60 mmol) of triethylamine in 200 mL of tetrahydrofuran was added dropwise 10.0 g (55 mmol) of trichloroacetyl chloride at temperature of 5° to 15° C. After being stirred for 3 hours at ambient temperature, the reaction mixture was poured into water, and then the mixture was extracted with ethyl acetate. The organic layer separated was washed with water and then with brine, dried on anhydrous sodium sulfate and then concentrated in vacuo. The resulting crude crystals were recrystallized from ethanol to give 14.0 g (40 mmol) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer separated
  3. washwas washed with water
  4. dry with materialwith brine, dried on anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-4874c90b9eff49d0b491d0986763490c
Source dataset
uspto-grants-1996_09
Patent number
US05556860

Reaction notes

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