Triethylamine → Tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamate

HRID 606063Notes

Reaction equation

HRID 606063 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:22][CH2:23][CH2:24][NH2:25])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[C:26](=O)([O:32]C(C)(C)C)[O:27][C:28]([CH3:31])([CH3:30])[CH3:29]>ClCCl>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 86247617N-(2-chloro-3-nitroquinolin-4-yl)ethane-1,2-diamine

Product 1

HCID 86616881Tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (3.12 mL, 22.4 mmol) was added to a slurry of N-(2-chloro-3-nitroquinolin-4-yl)ethane-1,2-diamine (3.00 g, 11.2 mmol) in dichloromethane (80 mL). A solution of di-tert-butyl carbonate (2.95 g, 13.5 mmol) in dichloromethane (20 mL) was added over 5 minutes to the slurry. The solution was stirred at room temperature for three hours and then was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with dichloromethane. The organic layers were combined and washed with brine, dried over magnesium sulfate, filtered, and concentrated to an orange solid. The crude product was purified by flash chromatography (silica gel, 3:1 hexanes/ethyl acetate as the eluent) to afford tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamate (3.70 g) as a bright yellow solid.

Workup

  1. customwas partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an orange solid
  7. customThe crude product was purified by flash chromatography (silica gel, 3:1 hexanes/ethyl acetate as the eluent)

Sources & evidence

ORD record
ord-0222456098194ee8a8443a84aac4e7b4
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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