HCID 11053048, compound → 3-(Quinolin-3-yl)propanoic acid

HRID 653961Notes

Reaction equation

HRID 653961 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2>[OH-].[K+].CO.O.CO>[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:6]([CH2:5][CH2:4][C:3]([OH:16])=[O:2])[CH:7]=1

Participants

5

Reactant 1

HCID 11053048HCID 11053048, compound

Product 1

HCID 124157513-(Quinolin-3-yl)propanoic acidYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 23689386Potassium hydroxide methanolSolvent

Procedure

A solution of 3-quinolinepropanoic acid methyl ester (2.21 g, 10.3 mmol) in 10% KOH/MeOH (48.2 mL), H2O (20 mL) and methanol (134 mL) was stirred at room temperature for 3 h. Upon completion of reaction, the solution was concentrated and the aqueous residue was acidified to pH 5-6 with glacial HOAc. A crystalline solid formed which was filtered, washing with H2O until the filtrate was neutral and dried to give 3-quinolinepropanoic acid (1.84 g, 9.14 mmol) in 89% yield as a solid, mp 180°-181° C.

Workup

  1. customUpon completion of reaction
  2. concentrationthe solution was concentrated
  3. customA crystalline solid formed which
  4. filtrationwas filtered
  5. washwashing with H2O until the filtrate
  6. customdried

Sources & evidence

ORD record
ord-1f8acf9e3d334ad0bbffa06ae89c4a19
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

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