Acetic Acid → 8-nitro-2-(pyridin-3-yl)-4H-chromen-4-one

HRID 876524Notes

Reaction equation

HRID 876524 reaction equation
[C:1]([O:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=1[C:19](=[O:21])[CH3:20])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[OH-].[K+].OS(O)(=O)=O.CC(O)=O>N1C=CC=CC=1>[N+:16]([C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:10]=1[O:9][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[CH:20][C:19]2=[O:21])([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 584773042-Acetyl-6-nitrophenyl nicotinate

Product 1

HCID 584772518-nitro-2-(pyridin-3-yl)-4H-chromen-4-oneYield 35%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

2-acetyl-6-nitrophenyl nicotinate 5 (1.3 g, 4.4 mmol) was dissolved in pyridine (10 mL) and heated to 50° C. Finely powdered KOH (3.4 g, 6.1 mmol) was added in small portions. After cooling to room temperature the reaction mixture was concentrated to dryness. Concentrated H2SO4 (0.4 g, 4.4 mmol) and AcOH (3 mL) was added and the mixture was heated to 80° C. for 2 h. The reaction mixture was concentrated to dryness and the crude residue was purified by flash chromatography eluting with Pentane/EtOAc (5:1) to give 6 (410 mg, 35% yield).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. concentrationwas concentrated to dryness
  3. temperaturethe mixture was heated to 80° C. for 2 h
  4. concentrationThe reaction mixture was concentrated to dryness
  5. customthe crude residue was purified by flash chromatography
  6. washeluting with Pentane/EtOAc (5:1)

Sources & evidence

ORD record
ord-9a6207ac3bb846e89a4dabdec0da50a1
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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