Triethylamine → 2-{4-[2-(Quinoline-8-carboxamido)-ethyl]-phenyl}-propionic acid

HRID 1277674Notes

Reaction equation

HRID 1277674 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11](Cl)=[O:12])[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([CH3:30])[C:25]([O:27]CC)=[O:26])=[CH:20][CH:19]=1.C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([NH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:30])[C:25]([OH:27])=[O:26])=[CH:20][CH:19]=2)=[O:12])[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 14722777Quinoline-8-carbonyl chlorideHCID 20463406Ethyl 2-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride

Product 1

HCID 234530552-{4-[2-(Quinoline-8-carboxamido)-ethyl]-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.0 g Quinoline-8-carbonyl chloride (m.p. 156°-160° C.) are added to 6.0 g ethyl 2-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride in 50 ml methylene chloride and a solution of 7 ml triethylamine in 20 ml methylene chloride slowly added dropwise at 0° C. The reaction mixture is thereafter stirred for 2 hours at ambient temperature, subsequently shaken out 6 times with 2 N aqueous sodium hydroxide solution and twice with 2 N hydrochloric acid, and the methylene chloride phase is then dried and evaporated. The residue is taken up with diethyl ether, undissolved material is filtered off and the diethyl ether is evaporated. Ethyl 2-{4-[2-(quinoline-8-carboxamido)-ethyl]-phenyl}-propionate (oil) remains behind in a yield of 8.0 g (91% of theory). This ester is saponified with 2.0 g sodium hydroxide in 50 ml 80% ethanol by heating under reflux for 2 hours. The reaction mixture is thereafter evaporated to dryness, the residue is taken up in water and diethyl ether, the layers are separated and the aqueous layer acidified. The 2-{4-[2-(quinoline-8-carboxamido)-ethyl]-phenyl}-propionic acid obtained is again reprecipitated by dissolving in dilute aqueous sodium bicarbonate solution and acidifying with hydrochloric acid, whereafter it is recrystallized from 50% isopropanol and then from toluene. The yield is 2.3 g (31% of theory); m.p. 143°-144° C.

Workup

  1. dry with materialtwice with 2 N hydrochloric acid, and the methylene chloride phase is then dried
  2. customevaporated
  3. filtrationis filtered off
  4. customthe diethyl ether is evaporated
  5. temperatureby heating
  6. temperatureunder reflux for 2 hours
  7. customThe reaction mixture is thereafter evaporated to dryness
  8. customdiethyl ether, the layers are separated

Sources & evidence

ORD record
ord-38a9f93836da4e7e966074765c8d5c26
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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