Ethyl 2-bromo-2-phenylpropanoate → 2-Phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionic acid

HRID 616195Notes

Reaction equation

HRID 616195 reaction equation
[Na].Cl.[CH3:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:6][CH2:5]1.C([O:23][C:24](=[O:34])[C:25](Br)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26])C>CO>[C:27]1([C:25]([O:20][C:17]2[CH:16]=[CH:15][C:14]([CH:7]3[C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:4]([CH3:3])[CH2:5][CH2:6]3)=[CH:19][CH:18]=2)([CH3:26])[C:24]([OH:34])=[O:23])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 3778911Ethyl 2-bromo-2-phenylpropanoateHCID 5360545SodiumHCID 203714411-Methyl-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydroquinoline hydrochloride

Product 1

HCID 203714352-Phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.6 g. of sodium in 140 ml. of methanol is combined with 27.55 g. of 1-methyl-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydroquinoline hydrochloride. The mixture is agitated for 30 minutes at 20°, and then 25.7 g. of 2-bromo-2-phenylpropionic acid ethyl ester is added dropwise thereto and the mixture is refluxed thereafter for 4 hours. After concentrating the mixture by evaporation, the residue is combined with water and extracted with chloroform. From the organic phase, the ethyl ester of 2-phenyl-2-[4-(1-methyl-1,2,3,4-tetrahydro-4-quinolyl)-phenoxy]-propionic acid is obtained as a yellow oil; nD20 = 1.5738.

Workup

  1. temperaturethe mixture is refluxed
  2. waitfor 4 hours
  3. concentrationAfter concentrating the mixture
  4. customby evaporation
  5. extractionextracted with chloroform

Sources & evidence

ORD record
ord-f76f64737ec840809949afcc0cd84e3d
Source dataset
uspto-grants-1978_02
Patent number
US04072754

Reaction notes

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