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

HRID 1097597Notes

Reaction equation

HRID 1097597 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[C:23]([NH:30][CH2:31][CH2:32][NH2:33])([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CN(C=O)C>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:33][CH2:32][CH2:31][NH:30][C:23](=[O:24])[O:25][C:26]([CH3:28])([CH3:27])[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 187201N-BOC-ethylenediamineHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 86616881Tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamateYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Triethylamine (30.98 g, 306.1 mmol) was added to a solution of 2,4-dichloro-3-nitroquinoline (50.0 g, 204 mmol) in DMF (200 mL). A solution of N-Boc-ethylenediamine (32.7 g, 204 mmol) in DMF (100 mL) was then added in small portions. The reaction was stirred at room temperature, and then most of the DMF was removed under reduced pressure. Water (600 mL) was added to the residue, and the mixture was stirred for three hours. A solid formed and was isolated by filtration, washed with water, and dried under house vacuum to provide 71 g of tert-butyl 2-[(2-chloro-3-nitroquinolin-4-yl)amino]ethylcarbamate as a yellow solid. A portion of the material (15 g) was dissolved in dichloromethane (200 mL), and the resulting solution was washed with brine (2×100 mL) and deionized water (2×100 mL), dried over magnesium sulfate, filtered, concentrated under reduced pressure, and further dried on a vacuum pump for three days to provide 13.99 g of product.

Workup

  1. custommost of the DMF was removed under reduced pressure
  2. additionWater (600 mL) was added to the residue
  3. stirringthe mixture was stirred for three hours
  4. customA solid formed
  5. customwas isolated by filtration
  6. washwashed with water
  7. customdried under house vacuum

Sources & evidence

ORD record
ord-80caf528aa55472f8e1bfb82de3a059b
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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