Sodium Sulfate → tert-Butyl 2-(3-aminoquinolin-4-ylamino)ethylcarbamate

HRID 1371298Notes

Reaction equation

HRID 1371298 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[N+:8]([C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:20]=1[NH:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:18][CH:17]=[CH:16][CH:15]=2)([O-])=O>[Pt].C1(C)C=CC=CC=1>[NH2:8][C:11]1[CH:12]=[N:13][C:14]2[C:19]([C:20]=1[NH:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

5

Reactant 2

HCID 24436Sodium SulfateHCID 12016823tert-Butyl 2-(3-nitroquinolin-4-ylamino)ethylcarbamate

Product 1

HCID 12016824tert-Butyl 2-(3-aminoquinolin-4-ylamino)ethylcarbamateYield 80.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

Platinum on carbon (1 g of 10%) and sodium sulfate (2 g) were added to a slurry of tert-butyl N-[2-(3-nitroquinolin-4-yl)aminoethyl]carbamate (100 g, 0.30 mol) in toluene (500 mL). The mixture was placed under a hydrogen atmosphere at 50 psi (3.4×104 pascals) on a Parr apparatus at ambient temperature overnight. The reaction mixture was filtered. The filtrate was concentrated to provide 73 g of tert-butyl N-[2-(3-aminoquinolin-4-yl)aminoethyl]carbamate as a dark gold oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e8a491a8dccd4572a8844be164d1a77b
Source dataset
uspto-grants-2007_01
Patent number
US07157453B2

Reaction notes

Loading…