HCID 66650072, compound → HCID 11637961, compound

HRID 418815Notes

Reaction equation

HRID 418815 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:23])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21])=[O:11]>Cl.C(O)(=O)C.O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[O:11][C:4]3[C:3]([C:8](=[O:23])[CH:9]=2)=[CH:2][CH:7]=[CH:6][CH:5]=3)=[C:13]([N+:20]([O-:22])=[O:21])[CH:14]=1

Participants

5

Reactant 1

HCID 66650072HCID 66650072, compound

Product 1

HCID 11637961HCID 11637961, compoundYield 70.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1-(2-Hydroxyphenyl)-3-(4-methoxy-2-nitrophenyl)propane-1,3-dione (5.92 g, 18.77 mmol) was dissolved in a mixture of 48% HCl (2 mL) and acetic acid (35 mL) and heated at 100° C. for 1 h. The reaction mixture was cooled to rt, diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried and concentrated to give the crude compound, which was purified by column chromatography using 5% ethyl acetate in CH2Cl2 to give 2-(4-methoxy-2-nitrophenyl)-4H-chromen-4-one (3.92 g, 70%).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customto give the crude compound, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-4e673b8d58724e65bd3948d34e100720
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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