Sodium Dithionite → Tert-butyl 2-[(3-amino-2-chloroquinolin-4-yl)amino]ethylcarbamate

HRID 606064Notes

Reaction equation

HRID 606064 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[Cl:9][C:10]1[C:19]([N+:20]([O-])=O)=[C:18]([NH:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1>O>[NH2:20][C:19]1[C:10]([Cl:9])=[N:11][C:12]2[C:17]([C:18]=1[NH:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 86616881Tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamate

Product 1

HCID 86616882Tert-butyl 2-[(3-amino-2-chloroquinolin-4-yl)amino]ethylcarbamateYield 62.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Na2S2O4 (10.3 g, 50.4 mmol) in water (40 mL) was added to a solution of tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamate (3.70 g, 10.1 mmol). A white solid precipitated immediately and after 30 min the precipitate was removed by filtration. The filtrate was concentrated under reduced pressure, was diluted with saturated aqueous sodium bicarbonate, and was extracted with dichloromethane three times. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to a pale yellow oil. Purification by flash chromatography (silica gel, gradient elution with 2:1 to 1:1 hexanes/ethyl acetate) afforded tert-butyl 2-[(3-amino-2-chloroquinolin-4-yl)amino]ethylcarbamate (2.14 g) as a colorless oil.

Workup

  1. customA white solid precipitated immediately and after 30 min the precipitate
  2. customwas removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionwas diluted with saturated aqueous sodium bicarbonate
  5. extractionwas extracted with dichloromethane three times
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to a pale yellow oil
  10. customPurification
  11. washby flash chromatography (silica gel, gradient elution with 2:1 to 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-fe5cbc5da5ea4440bc6daf92dbb116ea
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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