Potassium Carbonate → Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate

HRID 2366680Notes

Reaction equation

HRID 2366680 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-].S(S([O-])=O)([O-])=O.[Na+].[Na+]>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 57447067Ethyl 5-(3-nitroquinolin-4-ylamino)pentanoate

Product 1

HCID 57447068Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoateYield 96.1%

Reagents, catalysts & solvents 4

HCID 24489Sodium DithioniteCatalystHCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 5-(3-nitroquinolin-4-ylamino)pentanoate (151 g, 476 mmol) in dichloromethane (1 L) was added to a solution of sodium hydrosulfite (248.5 g, 1.427 mol), potassium carbonate (259.3 g, 1.876 mol), and ethyl viologen dibromide (1.78 g, 4.75 mmol) in water (1 L), and the reaction was stirred overnight at ambient temperature. An analysis by TLC indicated the presence of starting material; additional sodium hydrosulfite (5.0 g, 29 mmol) was added to the reaction, which was stirred for one additional hour. The organic layer was separated, washed with water (3×), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 131.51 g of ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate.

Workup

  1. stirringwas stirred for one additional hour
  2. customThe organic layer was separated
  3. washwashed with water (3×)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1c588760b1d44ee7a9d6bd225ab0afeb
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…