Hydrochloric Acid → 5-[1-(4-Pentyloxycarbonylaminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

HRID 504031Notes

Reaction equation

HRID 504031 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[C:12]([CH2:19][CH:20]4[S:24][C:23](=[O:25])[NH:22][C:21]4=[O:26])[CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[CH2:10][CH2:9][C:8]2=[O:27])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:37]([O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[O:38].Cl>ClCCl>[CH2:40]([O:39][C:37]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:16]3[C:11](=[C:12]([CH2:19][CH:20]4[S:24][C:23](=[O:25])[NH:22][C:21]4=[O:26])[CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[CH2:10][CH2:9][C:8]2=[O:27])=[CH:28][CH:29]=1)=[O:38])[CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 69489Pentyl chloroformateHCID 866139395-[1-(4-Aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione

Product 1

HCID 580267145-[1-(4-Pentyloxycarbonylaminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dioneYield 489.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 g of 5-[1-(4-aminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione was suspended in dichloromethane (6 ml), and 4 ml of pyridine was added with ice cooling to form a solution. 0.26 g of amyl chloroformate was added to this solution, followed by stirring for 1 hour. 1 N hydrochloric acid was added to the reaction liquid, and extracted with ethyl acetate. The extract was washed twice with water and once with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1), and recrystallized from diisopropyl ether, giving 3.75 g (97% yield) of 5-[1-(4-pentyloxycarbonylaminobenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinolin-5-ylmethyl]thiazolidine-2,4-dione as a white powder.

Workup

  1. customto form a solution
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed twice with water and once with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1→1:1)
  7. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-74ef95b6b2834494be97ba1ae393d232
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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