Morpholine → HCID 86657431, compound

HRID 1191255Notes

Reaction equation

HRID 1191255 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-0c1c03477ef14b66a1dbb9126988f55d
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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