Lithium Hydroxide → 3-(Quinolin-6-yl)propanoic acid

HRID 655206Notes

Reaction equation

HRID 655206 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)C.[OH-].[Li+]>CO>[N:13]1[C:14]2[C:9](=[CH:8][C:7]([CH2:6][CH2:5][C:4]([OH:17])=[O:3])=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23003951Ethyl 3-(6-quinolinyl)propanoate

Product 1

HCID 229313053-(Quinolin-6-yl)propanoic acidYield 20.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-quinolin-6-yl-propionic acid ethyl ester (100 mg, 0.437 mmol) in methanol (2 mL) was added 4 M aqueous solution of lithium hydroxide (0.55 mL, 2.18 mmol). The reaction mixture was stirred at room temperature for 3 h then it was concentrated in vacuo, diluted with water, and treated with 1 N aqueous hydrochloric acid until pH 5. The aqueous layer was extracted with ethyl acetate (3×), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide 18 mg of product as a white solid. 1H NMR 500 MHz (DMSO) δ 2.67 (t, 2H), 3.02 (t, 2H), 7.50 (dd, 1H), 7.67 (dd, 1H), 7.78 (d, 1H), 7.94 (d, 1H), 8.29 (dd, 1H), 8.84 (dd, 1H); MS (m/z) 202 [M+H+]+.

Workup

  1. concentrationit was concentrated in vacuo
  2. additiondiluted with water
  3. additiontreated with 1 N aqueous hydrochloric acid until pH 5
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c580fdb9da6c4428b8def640f94129c8
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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