Hydrochloric Acid → 4-Phenylpyridine-3-carboxylic acid--hydrogen chloride (1/1)

HRID 1200036Notes

Reaction equation

HRID 1200036 reaction equation
[C:1]1([C:7]2[C:12]([C:13]([O:15]C)=[O:14])=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CO.[ClH:21]>C(OCC)(=O)C>[ClH:21].[C:1]1([C:7]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 12482255Methyl 4-phenylpyridine-3-carboxylate

Product 1

HCID 700442024-Phenylpyridine-3-carboxylic acid--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-phenylnicotinate [cp. Heterocycles 22, 151-157 (1984)](53 g, 0.25 mol), 5N aqueous NaOH solution (100 ml) and methanol (100 ml) are refluxed together with stirring for 1 h. The reaction solution is allowed to cool, acidified with concentrated HCl to pH 4 and evaporated to dryness in vacuo. The residue is slurried in hot ethanol (75 ml), filtered, and the filtrates are evaporated to dryness in vacuo. The residue obtained is slurried in cold ethyl acetate (30 ml), filtered and dried to give 4-phenylnicotinic acid hydrochloride, m.p. 239°-241°.

Workup

  1. temperatureto cool
  2. customevaporated to dryness in vacuo
  3. filtrationfiltered
  4. customthe filtrates are evaporated to dryness in vacuo
  5. customThe residue obtained
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-1535dea61a86488983c6617fdc6471cb
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

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