Nicotinoyl chloride → HCID 11573720, compound

HRID 884725Notes

Reaction equation

HRID 884725 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:15]([C:16](=[O:18])[CH:17]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1>N1C=CC=CC=1>[C:19]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:15]([C:16](=[O:18])[CH:17]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1

Participants

4

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 2290162H-1-BENZOPYRAN-2-ONE, 2-(4-HYDROXYPHENYL)-

Product 1

HCID 11573720HCID 11573720, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer were placed 2-(4-hydroxyphenyl)chromen-4-one (100 mg, 0.419 mmol), pyridine (5 mL) and nicotinoyl chloride (223 mg, 1.25 mmol). The reaction mixture was stirred for 24 h at rt under nitrogen. The solvent was removed under reduced pressure and crude product was purified by column chromatography using 50% EtOAc in hexane to give 100 mg of 4-(4-oxo-4H-chromen-2-yl)phenyl nicotinate (69%). MS (ES) m/z: 344.09 (M+1).

Workup

  1. customIn a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer
  2. customThe solvent was removed under reduced pressure and crude product
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1148b56248564b7daf7a7c152120a71c
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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