Sodium Formate → N-[3-(4-Chlorophenyl)-8-hydroxy-2-isopropyl-4-oxo-4H-chromen-7-yl]formamide

HRID 14471

Reaction equation

HRID 14471 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:8]([CH:13]([CH3:15])[CH3:14])[O:9]2)=[CH:4][CH:3]=1.[CH:24]([O-])=[O:25].[Na+]>C(O)=O>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([C:7]2[C:6](=[O:23])[C:5]3[C:10](=[C:11]([OH:12])[C:2]([NH:1][CH:24]=[O:25])=[CH:3][CH:4]=3)[O:9][C:8]=2[CH:13]([CH3:14])[CH3:15])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 2723810Sodium FormateHCID 687013867-Amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one

Product 1

HCID 59724241N-[3-(4-Chlorophenyl)-8-hydroxy-2-isopropyl-4-oxo-4H-chromen-7-yl]formamide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A stirred mixture of 7-amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one (1.1 g, 3.35 mmol) and sodium formate (0.23 g, 3.35 mmol) in formic acid (50 ml) is heated under reflux for 2 h. After cooling to room temperature, the reaction mixture is poured into ice/water (300 ml) with stirring. The resulting aqueous suspension is washed with ethyl acetate (2×100 ml). The combined organic layers are washed with water (3×100 ml) and brine (100 ml), dried (magnesium sulfate) and filtered. The solvent is removed by evaporation in vacuo to afford a dark brown oil. This is purified by flash chromatography (hexane/ethyl acetate=1:1, followed by 100% ethyl acetate) to afford the title compound.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 h
  3. washThe resulting aqueous suspension is washed with ethyl acetate (2×100 ml)
  4. washThe combined organic layers are washed with water (3×100 ml) and brine (100 ml)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customThe solvent is removed by evaporation in vacuo
  8. customto afford a dark brown oil
  9. customThis is purified by flash chromatography (hexane/ethyl acetate=1:1, followed by 100% ethyl acetate)

Sources & evidence

ORD record
ord-808de5774aaf47ca9c8db9011397b39c
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Linked notes

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