Carbon Dioxide → 2-Phenyl-6-quinolineacetic acid

HRID 1282957Notes

Reaction equation

HRID 1282957 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]=[CH:6]2.[Mg].[C:20](=[O:22])=[O:21].[Cl-].[NH4+]>C(OCC)C>[C:13]1([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][C:20]([OH:22])=[O:21])[CH:4]=3)[N:9]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 280Carbon Dioxide2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 215205546-(Bromomethyl)-2-phenylquinoline

Product 1

HCID 215205512-Phenyl-6-quinolineacetic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The Grignard compound is prepared in the customary manner from 5 g of 6-bromomethyl-2-phenyl-quinoline and magnesium in 30 ml of diethyl ether. It is added to a solution of solid carbon dioxide in 100 ml of diethyl ether. At the same time a further quantity of solid carbon dioxide is added in portions to the reaction solution. Thereafter, aqueous ammonium chloride solution is added to the reaction mixture and the whole is extracted with ethyl acetate. The organic phases are extracted with 2 N sodium carbonate solution. The sodium carbonate extracts are adjusted to pH 6 and extracted with ethyl acetate. These ethyl acetate layers are dried and evaporated. The residue, after recrystallisation from methanol-pentane, yields 2-phenyl-6-quinolineacetic acid of melting point 176-179°C.

Workup

  1. extractionthe whole is extracted with ethyl acetate
  2. extractionThe organic phases are extracted with 2 N sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThese ethyl acetate layers are dried
  5. customevaporated
  6. customThe residue, after recrystallisation from methanol-pentane

Sources & evidence

ORD record
ord-d7ebf64d79d34e6ea5a52577f3b34277
Source dataset
uspto-grants-1976_08
Patent number
US03973022

Reaction notes

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