Water → Tert-butyl 2-hydroxy-3-[(3-nitroquinolin-4-yl)amino]propylcarbamate

HRID 1364016Notes

Reaction equation

HRID 1364016 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][CH:24]([OH:34])[CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].O>CN(C)C=O.O1CCOCC1>[OH:34][CH:24]([CH2:23][NH:22][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])[CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10511887tert-butyl N-(3-amino-2-hydroxypropyl)carbamateHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 66958711Tert-butyl 2-hydroxy-3-[(3-nitroquinolin-4-yl)amino]propylcarbamateYield 97.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (72 g, 710 mmol) was added to a solution of 4-chloro-3-nitroquinoline (98.9 g, 474 mmol) in N,N-dimethylformamide (DMF) (1 L). A solution of tert-butyl 3-amino-2-hydroxypropylcarbamate (108.19 g, 569 mmol) in dioxane (800 mL) was slowly added, and the reaction was stirred overnight at ambient temperature and then poured into water (3 L) with continuous stirring. A precipitate formed and was isolated by filtration, washed with water, and dried for three days in a vacuum oven at 65° C. to provide 167.54 g of tert-butyl 2-hydroxy-3-[(3-nitroquinolin-4-yl)amino]propylcarbamate as a bright yellow powder.

Workup

  1. customA precipitate formed
  2. customwas isolated by filtration
  3. washwashed with water
  4. customdried for three days in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-e29db353a013467c842504ed08e54198
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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