Morpholine → HCID 23153304, compound

HRID 492684Notes

Reaction equation

HRID 492684 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([O:14]C2C=CC=CC=2)=O)[CH:6]=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>O1CCCC1>[NH2:25][C:23]1[CH:22]=[CH:21][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:14])[CH:6]=2)=[C:2]([Cl:1])[CH:24]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 23153541HCID 23153541, compound

Product 1

HCID 23153304HCID 23153304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A crude product of 4-(2-chloro-4-nitrophenoxy)-2-(phenoxycarbonylamino)pyridine (634.8 mg) was dissolved in tetrahydrofuran (6.5 ml), and then morpholine (0.942 ml) was added thereto at room temperature, followed by stirring overnight and evaporating the solvent under a reduced pressure. The resultant residue was dissolved in ethanol (20 ml)-water (5 ml), and then electrolytic iron powder (500 mg) and ammonium chloride (1 g) were added thereto, followed by heating under reflux for 1 hr. The reaction mixture was cooled down to room temperature, and filtered through celite to remove an insoluble portion, which was washed with ethyl acetate-tetrahydrofuran (1:1) and water. The organic layer of the filtrate was separated, washed with water and brine in this order, dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=95:5) to provide the titled compound (283.3 mg) as pale yellow powder.

Workup

  1. customat room temperature
  2. customevaporating the solvent under a reduced pressure
  3. dissolutionThe resultant residue was dissolved in ethanol (20 ml)-water (5 ml)
  4. additionelectrolytic iron powder (500 mg) and ammonium chloride (1 g) were added
  5. temperatureby heating
  6. temperatureunder reflux for 1 hr
  7. filtrationfiltered through celite
  8. customto remove an insoluble portion, which
  9. washwas washed with ethyl acetate-tetrahydrofuran (1:1) and water
  10. customThe organic layer of the filtrate was separated
  11. washwashed with water and brine in this order
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was evaporated
  14. customto give a residue, which
  15. customwas purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-dee1d35572cf4ec0a75d21481014ec35
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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