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

HRID 895786Notes

Reaction equation

HRID 895786 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].CCCCCC>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

6

Reactant 4

HCID 8058HexaneHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 12016823tert-Butyl 2-(3-nitroquinolin-4-ylamino)ethylcarbamateYield 92,088.602%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (66.8 g, 0.66 mmol) was added to a solution of tert-butyl (N-2-aminoethyl)carbamate (55.0 g, 0.34 mmol) in anhydrous dichloromethane (500 mL). 4-Chloro-3-nitroquinoline (68.2 g, 0.33 mmol) was slowly added. The reaction mixture exothermed. The reaction mixture was allowed to stir overnight The resulting precipitate was isolated by filtration and rinsed with water to provide a yellow solid. The filtrate was washed with water, dried over magnesium sulfate and then concentrated to provide a yellow solid. The two batches of solid were combined, slurried with hexane, filtered and then dried to provide 101 g of 1,1-dimethylethyl N-{2-[(3-nitroquinolin-4-yl)amino]ethyl)carbamate as a yellow solid.

Workup

  1. customwas isolated by filtration
  2. washrinsed with water
  3. customto provide a yellow solid
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto provide a yellow solid
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-afda7eaa21634e6386c3de636fc20c7c
Source dataset
uspto-grants-2005_07
Patent number
US06916925B1

Reaction notes

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