3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 131729354, compound

HRID 418873Notes

Reaction equation

HRID 418873 reaction equation
C1C([C:7]2[O:17][C:16]3[CH:15]=[C:14]([OH:18])[CH:13]=[C:12]([OH:19])[C:11]=3[C:9](=[O:10])[CH:8]=2)=CC=C(O)C=1.Cl.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1>N1C=CC=CC=1>[C:22]([O:19][C:12]1[CH:13]=[C:14]([O:18][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=2)[CH:15]=[C:16]2[C:11]=1[C:9](=[O:10])[CH:8]=[CH:7][O:17]2)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 5280443Apigenin

Product 1

HCID 131729354HCID 131729354, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

In a 500 mL round-bottomed flask fitted with magnetic stirrer were placed apigenin (4′,5,7-trihydroxyflavone (5 g, 18.50 mmol)) and pyridine (250 mL). The mixture was cooled at −10° C. and nicotinoyl chloride HCl (16.5 g, 92.70 mmol) was added. Then the reaction mixture was stirred for 24 h at rt under nitrogen. The solvent was removed under reduced pressure and the residue was dissolved in chloroform, which was washed with water and evaporated. The crude product was purified by crystallization from DCM-MeOH to give 7.5 g of 2-(4-nicotinoyloxy)phenyl)-oxo-4H-chromene-5,7-diyl dinicotinate (69%). MS (ES) m/z: 586.17 (M+1), 481.11, 293.70.

Workup

  1. customIn a 500 mL round-bottomed flask fitted with magnetic stirrer
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washwhich was washed with water
  5. customevaporated
  6. customThe crude product was purified by crystallization from DCM-MeOH

Sources & evidence

ORD record
ord-d7de810d18624be1b72d63bd93fc4fb2
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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