Water → Tert-butyl 3-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}benzylcarbamate

HRID 415474Notes

Reaction equation

HRID 415474 reaction equation
C(N(CC)CC)C.[C:8]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH2:24])[CH:18]=1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[Cl:25][C:26]1[C:35]([N+:36]([O-:38])=[O:37])=[C:34](Cl)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.O>CN(C=O)C>[Cl:25][C:26]1[C:35]([N+:36]([O-:38])=[O:37])=[C:34]([NH:24][CH2:23][C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=2)[CH2:16][NH:15][C:8](=[O:9])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2756043tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamateHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 86633722Tert-butyl 3-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}benzylcarbamateYield 115.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (12.5 mL, 0.0889 mol) and 1-(N-Boc-aminomethyl)-3-(aminomethyl)benzene (17.71 g, 74.94 mmol) were sequentially added to a solution of 2,4-dichloro-3-nitroquinoline (18.2 g, 0.0750 mol) in DMF (90 mL), and the reaction was stirred at room temperature under nitrogen for 1.5 hours. The reaction was poured into water (2 L), and the suspension was stirred for 15 minutes. Most of the water was decanted away from the resulting precipitate, which was dissolved in ethyl acetate (600 mL). The ethyl acetate was separated from a small amount of remaining water and then removed under reduced pressure. The resulting solid was dried under vacuum to provide 38.24 g of tert-butyl 3-{[(2-chloro-3-nitroquinolin-4-yl)amino]methyl}benzylcarbamate as a sticky, amber solid.

Workup

  1. stirringthe suspension was stirred for 15 minutes
  2. customMost of the water was decanted away from the resulting precipitate, which
  3. dissolutionwas dissolved in ethyl acetate (600 mL)
  4. customThe ethyl acetate was separated from a small amount of remaining water
  5. customremoved under reduced pressure
  6. customThe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-a29fa9796cda4623928c8ddbffcd198f
Source dataset
uspto-grants-2012_01
Patent number
US08088790B2

Reaction notes

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