Sodium Hydroxide → 5-(2-Phenyleth-1-Ynyl)Nicotinic Acid

HRID 1099607Notes

Reaction equation

HRID 1099607 reaction equation
C([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[N:7][CH:6]=1)C.[OH-].[Na+]>CO.O>[C:13]1([C:12]#[C:11][C:9]2[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=2)[C:4]([OH:19])=[O:3])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2779231Ethyl 5-(2-phenyleth-1-ynyl)nicotinate

Product 1

HCID 27792365-(2-Phenyleth-1-Ynyl)Nicotinic AcidYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-phenylethynyl-nicotinic acid ethyl ester (1.17 g, 4.64 mmol) in methanol (10 mL) was added 5 N aqueous sodium hydroxide (2 mL, 10 mmol). The mixture was stirred at room temperature for approximately 20 h, before the reaction mixture was diluted with water (3 mL) and extracted with hexanes/EtOAc (95/5) (10 mL). The aqueous solution was acidified with 1 N HCl to pH 4. The white precipitate that formed was collected by filtration, washed with water (2 mL), and dried under vacuum to provide the title compound as a white solid (987 mg, yield 95%). 1H NMR (300 MHz, d6-DMSO) δ 9.02 (d, J=1.8 Hz, 1H), 8.94 (d, J=2.4 Hz, 1H), 8.34 (dd, J=1.8, 2.4 Hz, 1H), 7.63-7.60 (m, 2H), 7.48-7.44 (m, 3H); ESI-MS m/z 223.9 (M+H)+.

Workup

  1. extractionextracted with hexanes/EtOAc (95/5) (10 mL)
  2. customThe white precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with water (2 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3ba4d682f66c46419216a84ff559d230
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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