Sodium Hydroxide → 3-(Quinolin-8-yl)benzoic acid

HRID 1626756Notes

Reaction equation

HRID 1626756 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16]C)=[O:15])[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([OH:16])=[O:15])[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4189037HCID 4189037, compound

Product 1

HCID 41889673-(Quinolin-8-yl)benzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

820 mg (3.11 mmol) of methyl 3-(quinolin-8-yl)benzoate was dissolved in 8.2 mL of THF, and a 1N aqueous sodium hydroxide solution (4.7 mL) was added thereto at room temperature. The mixture was stirred at 60° C. for 1.5 hours. Thereafter, the organic solvent was distilled off under reduced pressure, H2O was added to the resulting residue, and then dissolution was conducted. Thereafter, 1N hydrochloric acid was added to the resultant at 0° C., and the pH was adjusted to 4. The precipitated solids were collected by filtration and dried, thereby giving 711 mg of 3-(quinolin-8-yl)benzoic acid (yield: 92%).

Workup

  1. customat room temperature
  2. distillationThereafter, the organic solvent was distilled off under reduced pressure, H2O
  3. additionwas added to the resulting residue
  4. dissolutiondissolution
  5. additionThereafter, 1N hydrochloric acid was added to the resultant at 0° C.
  6. filtrationThe precipitated solids were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-a11fef8394b5422ba726bbd86266bb83
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

Loading…