Hydrochloric Acid → 2-Hydroxy-5-phenylnicotinic acid

HRID 1707085Notes

Reaction equation

HRID 1707085 reaction equation
NC=C(C1C=CC=CC=1)C=O.C(OC)(=O)CC(OC)=O.C[O-].[Na+].[O:24]=[C:25]1[C:30]([C:31]([O:33]C)=[O:32])=[CH:29][C:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:27][NH:26]1.Cl>CO>[O:24]=[C:25]1[C:30]([C:31]([OH:33])=[O:32])=[CH:29][C:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:27][NH:26]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 10082526Methyl 2-hydroxy-5-phenylpyridine-3-carboxylateHCID 10942334Sodium MethoxideHCID 853250603-Amino-2-phenyl-2-propenal

Product 1

HCID 103759752-Hydroxy-5-phenylnicotinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 25.49 g. of 3-amino-2-phenyl-2-propenal and 27.32 g. of dimethyl malonate is reacted with 18.36 g. of sodium methoxide in one liter of methanol. The solution is stirred for 2 hours at room temperature and then is heated at reflux temperature for 3 hours. The resulting mixture is cooled and filtered to collect the precipitate. The solid is suspended in water and acidified with 10% aqueous hydrochloric acid to give a white solid. The solid is collected and washed with water followed by ethanol to yield 18.0 g. of methyl 1,2-dihydro-2-oxo-5-phenyl-3-pyridinecarboxylate. The ester is hydrolyzed by heating at reflux temperature for 2.5 hours in the presence of concentrated hydrochloric acid to give the product of the Example, m.p. 296° C. dec.

Workup

  1. additionA mixture of 25.49 g
  2. temperatureis heated
  3. temperatureat reflux temperature for 3 hours
  4. temperatureThe resulting mixture is cooled
  5. filtrationfiltered
  6. customto collect the precipitate
  7. customto give a white solid
  8. customThe solid is collected
  9. washwashed with water
  10. customto yield 18.0 g
  11. temperatureby heating
  12. customto give the product of the Example, m.p. 296° C. dec.

Sources & evidence

ORD record
ord-045c3ac7e4c54ebf84e1c839cb23a328
Source dataset
uspto-grants-1980_06
Patent number
US04209626

Reaction notes

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