Morpholine → HCID 12152137, compound

HRID 1480828Notes

Reaction equation

HRID 1480828 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(#N)C.CN(C=O)C>[CH3:9][O:8][C:6]1[N:7]=[C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:3]=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 107977036-Chloro-2-methoxy-3-nitropyridine

Product 1

HCID 12152137HCID 12152137, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

To a solution of 6-chloro-2-methoxy-3-nitropyridine (283 mg, 1.5 mmol) in acetonitrile/DMF (2:1, 3 mL) was added morpholine (0.13 mL, 1.5 mmol) and triethylamine (0.21 mL, 1.5 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between water (30 mL) and EtOAc (30 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 20% cyclohexane in EtOAc to give the title compound (280 mg, 78%). 1H NMR (500 MHz, CDCl3): δ 8.28 (d, J=9.0 Hz, 1H), 6.16 (d, J=9.0 Hz, 1H), 4.04 (s, 3H), 3.82 (t, J=4.5 Hz, 4H), 3.71 (t, J=4.5 Hz, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between water (30 mL) and EtOAc (30 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with 20% cyclohexane in EtOAc

Sources & evidence

ORD record
ord-98c58d581aab43d0b3fe063135cb8fdf
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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