Sodium Hydroxide → HCID 19002335, compound

HRID 1742883Notes

Reaction equation

HRID 1742883 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:21]=[CH:20][C:14]=2[C:15]([O:17]CC)=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]>>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[N:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:21]=[CH:20][C:14]=2[C:15]([OH:17])=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 19002353HCID 19002353, compound

Product 1

HCID 19002335HCID 19002335, compoundYield 75%

Procedure

30% strength sodium hydroxide (2 ml) is added to a solution of ethyl 2-(3,4-dimethoxyphenyl)-6-phenylnicotinate (compound no. 309; 3.6 g; 0.01 mole) in 95% strength alcohol (100 ml). The reaction medium is heated for 2 h to 60°-70° C. The medium is concentrated under reduced pressure and the residue is dissolved in water (100 ml). The medium is acidified with concentrated hydrochloric acid (2 ml): a gum is released. The mixture is extracted with ethyl acetate (100 ml). The solution is washed with water (2×100 ml), dried over anhydrous magnesium sulphate and then concentrated under reduced pressure. A foam is obtained which is crystallized by trituration in ether (50 ml). After filtration and drying, a beige poser (2.6 g; yield=75%) is obtained, m.p. 178° C. Working in the same manner, the compounds of formula (IV"') in which Z3 is the hydroxyl group and R371 has the meanings indicated below, is obtained.

Workup

  1. temperatureThe reaction medium is heated for 2 h to 60°-70° C
  2. concentrationThe medium is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in water (100 ml)
  4. extractionThe mixture is extracted with ethyl acetate (100 ml)
  5. washThe solution is washed with water (2×100 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customA foam is obtained which
  9. customis crystallized by trituration in ether (50 ml)
  10. filtrationAfter filtration
  11. customdrying
  12. customa beige poser (2.6 g; yield=75%) is obtained
  13. customis obtained

Sources & evidence

ORD record
ord-4da52fd7d23143e58a1280f7ac862617
Source dataset
uspto-grants-1994_08
Patent number
US05342835

Reaction notes

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