Triethylamine → N2,N2-bis(4-methoxybenzyl)-N4-(2-methylpropyl)-3-nitroquinoline-2,4-diamine

HRID 1097563Notes

Reaction equation

HRID 1097563 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:26]=[CH:25][C:13]([CH2:14][NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.[CH3:27][CH:28]([CH3:52])[CH2:29][NH:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[C:33](OS(C(F)(F)F)(=O)=O)[C:32]=1[N+:49]([O-:51])=[O:50].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:15]([CH2:14][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:26][CH:25]=2)[C:33]2[C:32]([N+:49]([O-:51])=[O:50])=[C:31]([NH:30][CH2:29][CH:28]([CH3:52])[CH3:27])[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 714952Bis(4-methoxybenzyl)amineHCID 20087003[4-(2-Methylpropyl)amino-3-nitroquinolin-2-yl]trifluoromethanesulfonate

Product 1

HCID 86626284N2,N2-bis(4-methoxybenzyl)-N4-(2-methylpropyl)-3-nitroquinoline-2,4-diamine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethyl amine (40.4 mL, 0.290 mol) and N,N-bis(4-methoxybenzyl)amine (62.0 g, 242 mmol) were sequentially added to a solution of [4-(2-methylpropyl)amino-3-nitroquinolin-2-yl]trifluoromethanesulfonate (Nikolaides et al, U.S. Pat. No. 5,395,937, Example 1, 95.0 g, 242 mmol) in toluene (300 mL) at ambient temperature. The solution was stirred at ambient temperature for a few minutes, heated at reflux for two hours, and allowed to cool to ambient temperature. Ethyl acetate and saturated aqueous sodium bicarbonate (300 mL) were added. The organic layer was separated and washed twice with saturated aqueous sodium bicarbonate. The combined aqueous fractions were filtered to remove a solid, and the filtrate was extracted with ethyl acetate (3×150 mL). The combined extracts were washed once with saturated aqueous sodium bicarbonate. All organic fractions were then combined and dried over magnesium sulfate, filtered through a layer of CELITE filter agent, concentrated under reduced pressure, and further dried under high vacuum for three days to provide N2,N2-bis(4-methoxybenzyl)-N4-(2-methylpropyl)-3-nitroquinoline-2,4-diamine as a red oil, which was used without purification.

Workup

  1. customat ambient temperature
  2. temperatureheated
  3. temperatureat reflux for two hours
  4. temperatureto cool to ambient temperature
  5. customThe organic layer was separated
  6. washwashed twice with saturated aqueous sodium bicarbonate
  7. filtrationThe combined aqueous fractions were filtered
  8. customto remove a solid
  9. extractionthe filtrate was extracted with ethyl acetate (3×150 mL)
  10. washThe combined extracts were washed once with saturated aqueous sodium bicarbonate
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered through a layer of CELITE filter agent
  13. concentrationconcentrated under reduced pressure
  14. customfurther dried under high vacuum for three days

Sources & evidence

ORD record
ord-5385ebc3814a4b459eccca40e8d9303f
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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