Pyridine → HCID 11587248, compound

HRID 884728Notes

Reaction equation

HRID 884728 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:17][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10](=[O:18])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:19][C:20](OC(C)=O)=[O:21].N1C=CC=CC=1>O>[C:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:17][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10](=[O:18])[CH:9]=2)=[CH:6][CH:7]=1)(=[O:21])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 116300742-(4-Hydroxyphenyl)-4H-pyrano[2,3-b]pyridin-4-one

Product 1

HCID 11587248HCID 11587248, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer were placed 2-(4-hydroxy-phenyl)-pyrano[2,3-b]pyridin-4-one (212 mg, 0.89 mmol), Ac2O (99 mg, 0.97 mmol), and pyridine (5 mL). The reaction mixture was stirred for 24 h at room temperature. The reaction mixture was poured into water and extracted with EtOAc. The organic layer washed with water, dried and concentrated to afford 4-(4-oxo-4H-pyrano[2,3-b]pyridine-2-yl)phenyl acetate (240 mg, 96%). MS (ES) m/z: 282.89 (M+1), 281.92 (M); Mp. 167-169° C.

Workup

  1. customIn a 50 mL round-bottomed flask fitted with condenser and magnetic stirrer
  2. extractionextracted with EtOAc
  3. washThe organic layer washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec12ac9679234b93950c72f1f950a6c3
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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