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

HRID 2182279Notes

Reaction equation

HRID 2182279 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[N+:30]([O-:32])=[O:31]>ClCCl>[N+:30]([C:21]1[CH:22]=[N:23][C:24]2[C:29]([C:20]=1[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:28][CH:27]=[CH:26][CH:25]=2)([O-:32])=[O:31]

Participants

5

Reactant 3

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

Product 1

HCID 12016823tert-Butyl 2-(3-nitroquinolin-4-ylamino)ethylcarbamateYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (66.8 g, 0.33 mol) was added to a solution of tert-butyl N-(2-aminoethyl)carbamate (55.0 g, 0.34 mol) in anhydrous dichloromethane (500 mL). 4-Chloro-3-nitroquinoline (68.2 g, 0.33 mol) was slowly added and the reaction exothermed. The reaction mixture was allowed to stir at ambient temperature overnight. The resulting precipitate was isolated by filtration to provide product as a yellow solid. The filtrate was washed with water, dried over magnesium sulfate and then concentrated under vacuum. The resulting residue was slurried with hexane and filtered to provide additional product as a yellow solid. The two crops were combined to provide 101 g of tert-butyl N-[2-(3-nitroquinolin-4-yl)aminoethyl]carbamate as a yellow solid, m.p. 157-158.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customto provide product as a yellow solid
  3. washThe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. filtrationfiltered
  7. customto provide additional product as a yellow solid

Sources & evidence

ORD record
ord-81a0da3aebc541df8787eb093a137238
Source dataset
uspto-grants-2005_05
Patent number
US06897221B2

Reaction notes

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