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

HRID 655210Notes

Reaction equation

HRID 655210 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[N:9]2)C.[OH-].[Li+]>CO>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([CH2:5][C:4]([OH:16])=[O:3])=[CH:15][CH:14]=2)[N:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68705540Ethyl 2-(quinoxalin-6-YL)acetate

Product 1

HCID 184369162-(Quinoxalin-6-yl)acetic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of quinoxalin-6-yl-acetic acid ethyl ester (95 mg, 0.44 mmol) in methanol (2 mL) was added 4 M aqueous lithium hydroxide (0.55 mL, 2.2 mmol). The reaction mixture was stirred at room temperature for 17 h then it was concentrated in vacuo, diluted with water and extracted with diethyl ether (3×). The aqueous layer was treated with 1 N aqueous hydrochloric acid until pH 2 and extracted with ethyl acetate (3×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 64 mg of product as a beige solid. 1H NMR 500 MHz (DMSO) δ 3.90 (s, 2H), 7.78 (dd, 1H), 7.99 (d, 1H), 8.06 (d, 1H), 8.93 (dd, 2H); MS (m/z) 189 [M+H+]+.

Workup

  1. concentrationit was concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with diethyl ether (3×)
  4. additionThe aqueous layer was treated with 1 N aqueous hydrochloric acid until pH 2
  5. extractionextracted with ethyl acetate (3×)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1cc9c4738784d9cab790e4673a01c0b
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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