Potassium Carbonate → 2-[4-(2-quinolyloxy)phenoxy]propionic acid N,N-dimethylamide

HRID 1249110Notes

Reaction equation

HRID 1249110 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:4][CH:3]=1.[CH3:19][N:20]([CH3:26])[C:21](=[O:25])[CH:22](Br)[CH3:23].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:19][N:20]([CH3:26])[C:21](=[O:25])[CH:22]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)=[CH:17][CH:18]=1)[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113673482-BROMO-N,N-DIMETHYLPROPANAMIDEHCID 137473862-(4-Hydroxyphenoxy)quinoline

Product 1

HCID 137473902-[4-(2-quinolyloxy)phenoxy]propionic acid N,N-dimethylamideYield 88%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In 100 ml of methyl ethyl ketone, 2.3 g of the intermediate of Preparation 1 of 2-(4-hydroxyphenoxy)quinoline, 1.8 g of N,N-dimethyl-α-bromopropionic acid amide and 1.4 g of potassium carbonate were added and the mixture was refluxed for 5 hours. After the reaction, the precipitated crystal was separated by a filtration and the solvent was distilled off and the product was dried under a reduced pressure. The resulting crude crystal was recrystallized from a solvent of methanol-water to obtain 3.6 g (yield 88%) of white crystal of the object compound.

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 5 hours
  3. customAfter the reaction
  4. customthe precipitated crystal was separated by a filtration
  5. distillationthe solvent was distilled off
  6. customthe product was dried under a reduced pressure
  7. customThe resulting crude crystal was recrystallized from a solvent of methanol-water

Sources & evidence

ORD record
ord-91654c826c5f4595b94c36831121921d
Source dataset
uspto-grants-1986_12
Patent number
US04629493

Reaction notes

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