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

HRID 987192Notes

Reaction equation

HRID 987192 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. customThe resulting precipitate was 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-306098ad0a1146a6808858b741ecbc61
Source dataset
uspto-grants-2003_10
Patent number
US06630588B2

Reaction notes

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