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

HRID 1811440Notes

Reaction equation

HRID 1811440 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-8522019063964cd2bd61512440129753
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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