Water → N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine

HRID 1097553

Reaction equation

HRID 1097553 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.[NH2:23][CH2:24][C:25]([NH2:28])([CH3:27])[CH3:26].O>CN1CCCC1=O>[Cl:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH:23][CH2:24][C:25]([CH3:27])([NH2:28])[CH3:26])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 27851382,4-Dichloro-3-nitroquinoline

Product 1

HCID 86227765N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

Triethylamine (75 mL, 0.54 mol) was slowly added to a solution of 2,4-dichloro-3-nitroquinoline (André et al, U.S. Pat. No. 4,988,815, Example 2, 114 g, 0.470 mol) in anhydrous 1-methyl-2-pyrrolidinone (NMP) (450 mL), and the resulting black solution was cooled to 0° C. A solution of 1,2-diamino-2-methylpropane (42 g, 0.54 mol) in anhydrous NMP (42 mL) was added dropwise over a period of three hours. After the addition was complete, the reaction was allowed to warm to ambient temperature, stirred for five hours, and poured slowly into warm water (4 L) with vigorous stirring. A yellow precipitate formed, and the suspension was stirred for one hour at ambient temperature. The precipitate was isolated by filtration and washed with cold water until the filtrate was colorless. The solid was dissolved in dichloromethane (4 L), and the resulting solution was washed sequentially with saturated aqueous sodium carbonate and brine, dried over magnesium sulfate and sodium sulfate, filtered through a layer of CELITE filter agent, and concentrated under reduced pressure to provide 130 g of N1-(2-chloro-3-nitroquinolin-4-yl)-2-methylpropane-1,2-diamine as a bright yellow powder.

Workup

  1. additionAfter the addition
  2. additionpoured slowly
  3. customA yellow precipitate formed
  4. stirringthe suspension was stirred for one hour at ambient temperature
  5. customThe precipitate was isolated by filtration
  6. washwashed with cold water until the filtrate
  7. dissolutionThe solid was dissolved in dichloromethane (4 L)
  8. washthe resulting solution was washed sequentially with saturated aqueous sodium carbonate and brine
  9. dry with materialdried over magnesium sulfate and sodium sulfate
  10. filtrationfiltered through a layer of CELITE filter agent
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-489fbcf52ceb43719bcce3ccbb055541
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Linked notes

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