Morpholine → HCID 86657431, compound

HRID 1481592Notes

Reaction equation

HRID 1481592 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-584cc84bb0ce4a2982466525af50d80e
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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