Hexane → HCID 57677741, compound

HRID 492752Notes

Reaction equation

HRID 492752 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].C(OCC)(=O)C.O1CCCC1.CCCCCC>C(O)C.O.C(OCC)C.[Fe]>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

9

Reactant 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 21939870Tetrahydrofuran ethyl acetateHCID 57677759N-[4-(4-nitrophenoxy)-2-pyridinyl]-4-morpholinecarboxamide

Product 1

HCID 57677741HCID 57677741, compoundYield 59.3%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Morpholine-4-carboxylic acid [4-(4-nitrophenoxy)pyridin-2-yl]amide (227 mg) was dissolved in ethanol (10 ml)-water (2 ml), and then electrolytic iron powder (150 mg) and ammonium chloride (300 mg) were added thereto, followed by heating under reflux for 1 hr. The reaction mixture was cooled down to room temperature, and then ethyl acetate-tetrahydrofuran (1:1) was added, followed by stirring. The mixture was filtered through celite to remove an insoluble portion, which was washed with ethyl acetate and water. The organic layer of the filtrate was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; hexane:ethyl acetate=1:5, then ethyl acetate). Fractions containing the target compound were concentrated under a reduced pressure to give a residue, which was then suspended in diethyl ether (6 ml)-hexane (12 ml). The solid was filtered, and dried under aeration to provide the titled compound (81.3 mg, 59.3%) as a pale yellow solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hr
  3. filtrationThe mixture was filtered through celite
  4. customto remove an insoluble portion, which
  5. washwas washed with ethyl acetate and water
  6. washThe organic layer of the filtrate was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under a reduced pressure
  9. customto give a residue, which
  10. customwas then purified by silica gel column chromatography (eluent
  11. additionFractions containing the target compound
  12. concentrationwere concentrated under a reduced pressure
  13. customto give a residue, which
  14. filtrationThe solid was filtered
  15. customdried under aeration

Sources & evidence

ORD record
ord-10a5fd1049bb44e08c20777345bb7b8c
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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