HCID 53944765, compound → HCID 54172313, compound

HRID 1707295Notes

Reaction equation

HRID 1707295 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([O:22][CH3:23])=[O:21])[N:15]=2)=[O:13])[CH:9]=[CH:8][C:7]=1[O:24]C>Br>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([O:22][CH3:23])=[O:21])[N:15]=2)=[O:13])[CH:9]=[CH:8][C:7]=1[OH:24]

Participants

3

Reactant 1

HCID 53944765HCID 53944765, compound

Product 1

HCID 54172313HCID 54172313, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1.3g of 3-[5-(6-methoxycarbonyl-2-pyridylcarbonyl)-2-methoxyphenyl]-propionic acid methyl ester is refluxed in 12 ml of 62% hydrobromic acid for 12 hours. The reaction mixture is poured on ice/water, the precipitate is suctioned off and dried. The crude product (1.2g) is refluxed in 11 ml of methanol with 3 drops of concentrated sulfuric acid and concentrated by evaporation. The residue is taken up in ethyl acetate, shaken out with 10% sodium bicarbonate solution, washed with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/ethyl acetate (0-40%). 640 mg of 3-[5-(6-methoxycarbonyl-2-pyridylcarbonyl)-2-hydroxyphenyl]-proPionic acid methyl ester of melting point 121°-122° C. is obtained.

Workup

  1. additionThe reaction mixture is poured on ice/water
  2. customdried
  3. temperatureThe crude product (1.2g) is refluxed in 11 ml of methanol with 3 drops of concentrated sulfuric acid
  4. concentrationconcentrated by evaporation
  5. washwashed with saturated common salt solution
  6. customdried on sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customThe residue is chromatographed on silica gel with hexane/ethyl acetate (0-40%)

Sources & evidence

ORD record
ord-1df42ee3f45e4066b15191914df54f8e
Source dataset
uspto-grants-1994_10
Patent number
US05352701

Reaction notes

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