Water → tert-Butyl 2-(3-nitroquinolin-4-ylamino)ethylcarbamate

HRID 1364026Notes

Reaction equation

HRID 1364026 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].[NH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].O>CN(C=O)C>[N+:19]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:9]=1[NH:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[CH:17][CH:16]=[CH:15][CH:14]=2)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 12016823tert-Butyl 2-(3-nitroquinolin-4-ylamino)ethylcarbamateYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (58.2 g, 575 mmol) and 4-chloro-3-nitroquinoline (80.0 g, 384 mmol) were added to a solution of tert-butyl N-(2-aminoethyl)carbamate (67.6 g, 422 mmol) in DMF (300 mL), and the reaction was stirred overnight at ambient temperature. Water (600 mL) was added, and the resulting mixture was stirred for one hour. A precipitate formed and was isolated by filtration, washed with water (3×150 mL), and dried for two days in a vacuum oven at 45° C. to provide 125.36 g of tert-butyl 2-[(3-nitroquinolin-4-yl)amino]ethylcarbamate as a yellow solid.

Workup

  1. stirringthe resulting mixture was stirred for one hour
  2. customA precipitate formed
  3. customwas isolated by filtration
  4. washwashed with water (3×150 mL)
  5. customdried for two days in a vacuum oven at 45° C.

Sources & evidence

ORD record
ord-81e8b949115d45b3be35e2793544f49e
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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