Sulfuric Acid → 2-Phenyl-6-quinolineacetic acid

HRID 1282949Notes

Reaction equation

HRID 1282949 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:17]C#N)[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[C:25](=[O:28])(O)[O-:26].[Na+]>O.C(O)(=O)C>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:17][C:25]([OH:26])=[O:28])[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 215205492-Phenyl-6-quinolineacetonitrile

Product 1

HCID 215205512-Phenyl-6-quinolineacetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A mixture of 10 g of 2-phenyl-6-quinolineacetonitrile, 19 ml of water, 19 ml of concentrated sulphuric acid and 19 ml of glacial acetic acid is kept under reflux for 2 hours. Thereafter, ice and water are added and the pH is adjusted to 5-6 with solid sodium bicarbonate. The crystals which thereupon precipitate are filtered off and rinsed with water. Recrystallisation from methanol-ether-petroleum ether yields 2-phenyl-6-quinolineacetic acid of melting point 176°-179°C. 2-(p-Chlorophenyl)-6-quinoline-acetic acid and 2-(p-fluorophenyl)-6-quinolineacetic acid are obtained analogously.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe crystals which thereupon precipitate are filtered off
  3. washrinsed with water
  4. customRecrystallisation from methanol-ether-petroleum ether

Sources & evidence

ORD record
ord-3caee60623554e8bbbabe55311bf679a
Source dataset
uspto-grants-1976_08
Patent number
US03973022

Reaction notes

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