Water → 2-(6-methylquinolin-2-yl)benzoic Acid

HRID 1956762Notes

Reaction equation

HRID 1956762 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])[CH:6]=[CH:5]2.O.[OH-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([OH:16])=[O:15])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15816898HCID 15816898, compound

Product 1

HCID 98816992-(6-methylquinolin-2-yl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

7.08 g (25.5 mmol) of methyl 2-(6-methylquinolin-2-yl)benzoate obtained in Example 5 was suspended in 75 ml of methanol and 35 ml of water in which 3.06 g (76.6 mmol) of sodium hydroxide was dissolved was added thereto. After heating at 60° C. for 3 hours, the reaction mixture was concentrated under reduced pressure and 200 ml of water was added to the residue. The resulting solution was acidified with 2N hydrochloric acid and the thus formed precipitate was collected by filtration. The precipitate was washed with water and dried to obtain 2-(6-methylquinolin-2-yl)benzoic acid. NMR (270 MHz, CD3OD):

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated under reduced pressure and 200 ml of water
  3. additionwas added to the residue
  4. filtrationthe thus formed precipitate was collected by filtration
  5. washThe precipitate was washed with water
  6. customdried

Sources & evidence

ORD record
ord-04983a0cd1dd49caa98bbf5572441e61
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

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