Sodium Hydroxide → 2-Phenyl-6-quinolineacetic acid

HRID 1282955Notes

Reaction equation

HRID 1282955 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][CH:18]=[O:19])[CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:20].[Na+]>C(O)C.O.[N+]([O-])([O-])=O.[Ag+]>[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([CH2:17][C:18]([OH:20])=[O:19])[CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 544780362-Phenyl-6-quinolineacetaldehyde

Product 1

HCID 215205512-Phenyl-6-quinolineacetic acid

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.5 g of crude 2-phenyl-6-quinolineacetaldehyde in 3 ml of ethanol is slowly added dropwise at room temperature to a suspension of 3.4 g of silver nitrate and 1.6 g of sodium hydroxide in 12 ml of water. After completion of the addition, the mixture is stirred for a further 3 hours. Thereafter the suspension is clarified by filtration and the filtrate is washed with ether and adjusted to a pH of 6. The emulsion thereby produced is extracted with ethyl acetate. The ethyl acetate extracts, after drying, evaporation and recrystallisation of the residue from methanol-pentane, yield 2-phenyl-6-quinolineacetic acid of melting point 176°-179°C.

Workup

  1. additionAfter completion of the addition
  2. filtrationThereafter the suspension is clarified by filtration
  3. washthe filtrate is washed with ether
  4. customThe emulsion thereby produced
  5. extractionis extracted with ethyl acetate
  6. customafter drying
  7. customevaporation and recrystallisation of the residue from methanol-pentane

Sources & evidence

ORD record
ord-f3106592f8e24746b3a1b389ac828bc1
Source dataset
uspto-grants-1976_08
Patent number
US03973022

Reaction notes

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