Morpholine → HCID 86657431, compound

HRID 570272Notes

Reaction equation

HRID 570272 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=[C:4]([Cl:12])[N:3]=1.C([O-])([O-])=O.[K+].[K+].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CN(C=O)C.O>[Cl:12][C:4]1[N:3]=[C:2]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH2:11])[CH:5]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 2827402,6-Dichloro-3-nitropyridin-4-amine

Product 1

HCID 86657431HCID 86657431, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dichloro-3-nitro-pyridin-4-ylamine (970 mg, 4.66 mmol) in DMF (5 mL), K2CO3 (3.20 g, 23.0 mmol) was added, followed by addition of morpholine (0.410 mL, 4.60 mmol). The resulting mixture was stirred at room temperature for 2 h. The resulting mixture was diluted with water and extracted with EtOAc (3×10 mL). The organic layers were combined, dried (Na2SO4) and concentrated. The resulting residue was purified on silica (0:100-50:50 EtOAc-hexanes) to yield 6-chloro-2-morpholin-4-yl-3-nitro-pyridin-4-ylamine. 1H-NMR (400 MHz, CDCl3) δ: 5.99-6.20 (m, 3H), 3.72-3.82 (m, 4H), 3.40-3.50 (m, 4H).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe resulting residue was purified on silica (0:100-50:50 EtOAc-hexanes)

Sources & evidence

ORD record
ord-f051820c4afa4df59da4f354e57c7de5
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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