Methanol → HCID 54378725, compound

HRID 1282954Notes

Reaction equation

HRID 1282954 reaction equation
[CH3:1][CH:2]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH:10]=[CH:9]2)[C:3]([OH:5])=[O:4].[CH3:23]O>S(=O)(=O)(O)O>[CH3:23][O:4][C:3](=[O:5])[CH:2]([CH3:1])[C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 887MethanolHCID 21520541HCID 21520541, compound

Product 1

HCID 54378725HCID 54378725, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A mixture consisting of 1.9 g of α-methyl-2-(p-chlorophenyl)-6-quinolineacetic acid, 28 ml of methanol and 28 drops of concentrated sulphuric acid is kept for 2 hours under reflux. Thereafter the reaction mixture is concentrated on a rotary evaporator. The residue is treated with ice, ehter and 50 ml of 0.5 N sodium chloride solution. After thorough shaking, the aqueous phase is separated off and the organic phase is washed with water, dried over sodium sulphate and evaporated. The residue is dissolved in 25 ml of ethyl acetate and treated with petroleum ether until it crystallises. α-Methyl-2-(p-chlorophenyl)-6-quinolineacetic acid methyl ester of melting point 114°-115°C is obtained.

Workup

  1. temperatureunder reflux
  2. concentrationThereafter the reaction mixture is concentrated on a rotary evaporator
  3. additionThe residue is treated with ice, ehter and 50 ml of 0.5 N sodium chloride solution
  4. customAfter thorough shaking, the aqueous phase is separated off
  5. washthe organic phase is washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. dissolutionThe residue is dissolved in 25 ml of ethyl acetate
  9. additiontreated with petroleum ether until it
  10. customcrystallises

Sources & evidence

ORD record
ord-b6073a8abfb440be8d46b5f65f259559
Source dataset
uspto-grants-1976_08
Patent number
US03973022

Reaction notes

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