Sodium Hydroxide → 2-(Quinoxalin-6-yl)acetic acid

HRID 1921655Notes

Reaction equation

HRID 1921655 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][CH:15]=[N:14]2)C(OCC)=O)C.[OH-].[Na+]>CO>[N:17]1[C:18]2[C:13](=[CH:12][C:11]([CH2:5][C:4]([OH:21])=[O:3])=[CH:20][CH:19]=2)[N:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 674275872-Quinoxalin-6-yl-malonic acid diethyl ester

Product 1

HCID 184369162-(Quinoxalin-6-yl)acetic acidYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-iodo-quinoxaline (0.323 g, 1.26 mmol), malonic acid diethyl ester (0.404 g, 2.52 mmol), copper iodide (0.012 g, 0.063 mmol), biphenyl-2-ol (0.021 g, 0.126 mmol) and cesium carbonate (0.616 g, 1.89 mmol) in THF (5 mL) was heated to 70° C. in a sealed tube for 24 hours. The solution was then cooled to room temperature, water was added and the crude product was extracted from ethyl acetate. The product was purified via silica gel column chromatography in hexane:ethyl acetate (1:1) to give 2-quinoxalin-6-yl-malonic acid diethyl ester. 2-quinoxalin-6-yl-malonic acid diethyl ester (0.066 g, 0.229 mmol) was added to a solution of sodium hydroxide [2N] (0.229 mL) in methanol (2 mL) and stirred for several hours at room temperature. The reaction was then evaporated in vacuo, 1N HCl was added and the product was extracted with ethyl acetate to give 0.030 g (70%) of quinoxalin-6-yl-acetic acid. 1H NMR (400 MHz, DMSO-d6) δ 12.6 (bs, 1H), 8.93 (dd, 2H, J=2.0, 6.0 Hz), 8.05 (d, 1H, 8.8 Hz), 7.99 (m, 1H), 7.79 (dd, 1H, J=2.0, 8.8 Hz), 3.89 (s, 2H).

Workup

  1. customThe reaction was then evaporated in vacuo, 1N HCl
  2. additionwas added
  3. extractionthe product was extracted with ethyl acetate

Sources & evidence

ORD record
ord-5d8ad14ff1844f61a8bfe4ec3590006d
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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