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

HRID 1364027Notes

Reaction equation

HRID 1364027 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][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O.ClCCl>[Pt].CO>[NH2:1][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 12016823tert-Butyl 2-(3-nitroquinolin-4-ylamino)ethylcarbamate

Product 1

HCID 12016824tert-Butyl 2-(3-aminoquinolin-4-ylamino)ethylcarbamateYield 86%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 2-[(3-nitroquinolin-4-yl)amino]ethylcarbamate (20.0 g, 60.2 mmol) in a 2:1 mixture of dichloromethane:methanol (500 mL) was added to a Parr vessel. The system was purged with nitrogen, and 5% platinum on carbon (7.04 g, 36.1 mmol) was added. The vessel was placed under hydrogen pressure (50 psi, 3.4×105 Pa) and shaken overnight. The reaction mixture was filtered and concentrated under reduced pressure to provide 15.65 g of tert-butyl 2-[(3-aminoquinolin-4-yl)amino]ethylcarbamate.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f6f64b781dc477a8f0e61f473fc6699
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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