Sodium Hydroxide → 2-Ethoxy-5-[(4-ethylpiperazino)sulfonyl]nicotinic acid

HRID 1831479Notes

Reaction equation

HRID 1831479 reaction equation
[CH2:1]([O:3][C:4]1[N:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[CH:11][C:5]=1[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[N:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]2)(=[O:16])=[O:17])=[CH:11][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10109777Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

Product 1

HCID 46689282-Ethoxy-5-[(4-ethylpiperazino)sulfonyl]nicotinic acidYield 43.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate (10.2 g, 0.0275 mol) was dissolved in toluene (50 mL) and a solution of sodium hydroxide (1.1 g, 0.0275 mol) in water (20 mL) added to it. This two phase mixture was then stirred vigorously at ambient temperature overnight. The aqueous phase was separated off and adjusted to pH=5.6 by addition of conc. hydrochloric acid. The precipitated product was slurried with ice cooling for 15 minutes, filtered, water washed and dried under vacuo at 50° C. to afford the title compound (4.1 g, 43%) as an off-white solid. Mpt 206–207° C. δ (CDCl3): 1.25 (3H, t), 1.39 (3H, t), (2H, q), 3.03 (4H, m), 3.25 (4H, m), 4.50 (2H, q), 8.25 (1H, d), 8.56 (1H, d). m/z (Found: 344 [M+H]+, 100%. C14H22N3O5S requires 344.38).

Workup

  1. customThe aqueous phase was separated off
  2. additionadjusted to pH=5.6 by addition of conc. hydrochloric acid
  3. waitThe precipitated product was slurried with ice cooling for 15 minutes
  4. filtrationfiltered
  5. washwater washed
  6. customdried under vacuo at 50° C.

Sources & evidence

ORD record
ord-ac2d1af141304dff8847bd5f1af4d032
Source dataset
uspto-grants-2006_06
Patent number
US07067660B2

Reaction notes

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