Water → HCID 9965512, compound

HRID 884419Notes

Reaction equation

HRID 884419 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[N:12]1([CH2:18][CH2:19][CH2:20][NH2:21])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[N:12]1([CH2:18][CH2:19][CH2:20][NH:21][C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61055N-(3-Aminopropyl)morpholineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 9965512HCID 9965512, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (1.3 g, 7.0 mmol), 3-(4-morpholinyl)-1-aminopropane (3.1 g, 20 mmol), and K2CO3 (3.0 g, 22 mmol) in DMF (20 mL) was stirred at 110° C. for 18 h. The reaction mixture was cooled to room temperature, poured into water (200 mL) and extracted with CH2Cl2 (100 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 90/10 EtOAc/MeOH) to yield the product as an orange solid (0.45 g, 23%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with CH2Cl2 (100 mL)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 90/10 EtOAc/MeOH)

Sources & evidence

ORD record
ord-8e98e52e712d499fa53645d173867293
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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