Sodium Hydroxide → Carboxystyrylpyridine

HRID 989909Notes

Reaction equation

HRID 989909 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>C1COCC1>[CH:10]([C:5]1[N:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:18])=[O:2])=[CH:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 536734442-Styrylnicotinic acid methyl ester

Product 1

HCID 54028018CarboxystyrylpyridineYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the ester 19 (55.0 g, 0.23 mol) in THF (100 mL) was treated with a 3 N NaOH solution (110 mL, 0.25 mol) for 21 h at ambient temperature. After removal of solvents, the residue was taken up in water and ethyl ether. The phases were separated, and the aqueous phase was washed with ether (2×). The resulting aqueous phase was neutralized with a 2 N HCl solution, and the precipitate was then collected by filtration to afford the acid 20 (50.2 g, 97%) as a cream solid:

Workup

  1. customAfter removal of solvents
  2. customThe phases were separated
  3. washthe aqueous phase was washed with ether (2×)
  4. filtrationthe precipitate was then collected by filtration

Sources & evidence

ORD record
ord-87e2992105254cf0bed65c794d9f2958
Source dataset
uspto-grants-2002_10
Patent number
US06458816B1

Reaction notes

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