Lithium Hydroxide → HCID 59320364, compound

HRID 655203Notes

Reaction equation

HRID 655203 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:16])[CH:10]=[CH:9]2)C.[OH-].[Li+]>CO>[CH3:16][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH2:5][C:4]([OH:17])=[O:3])[CH:7]=2)[N:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68706572HCID 68706572, compound

Product 1

HCID 59320364HCID 59320364, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2-methyl-quinolin-6-yl)-acetic acid ethyl ester (100 mg, 0.436 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 14 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 19 mg of product as a light beige solid. 1H NMR 500 MHz (DMSO) δ 2.65 (s, 3H), 3.76 (s, 2H), 7.40 (d, 1H), 7.60 (dd, 1H), 7.77 (d, 1H), 7.86 (d, 1H), 8.20 (d, 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-4ccdb9c03d564078b07c4ac3281f545e
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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