Ammonium Chloride → HCID 23153283, compound

HRID 492668Notes

Reaction equation

HRID 492668 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=2[F:22])[CH:9]=[CH:8][N:7]=1)=[O:4].[Cl-].[NH4+].C(OCC)(=O)C.O1CCCC1.C(OCC)C.CCCCCC>C(O)C.O.[Fe]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:5][C:3]([N:2]([CH3:23])[CH3:1])=[O:4])[CH:11]=2)=[C:14]([F:22])[CH:15]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 21584099Diethylether hexaneHCID 21939870Tetrahydrofuran ethyl acetateHCID 23153179HCID 23153179, compound

Product 1

HCID 23153283HCID 23153283, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-[(Dimethylamino)carbonylamino]-4-(2-fluoro-4-nitrophenoxy)pyridine (218 mg) was dissolved in ethanol (20 ml)-water (5 ml) to dissolve, and then electrolytic iron powder (250 mg) and ammonium chloride (500 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 thereto, followed by stirring. An insoluble portion was filtered through celite, and washed with ethyl acetate and water. The organic layer of the filtrate was separated, washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, to which thus diethyl ether-hexane was then added to suspend. Crystals was filtered off and dried under aeration to provide the titled compound (180 mg, 91%) as pale yellow crystals.

Workup

  1. dissolutionto dissolve
  2. temperatureby heating
  3. temperatureunder reflux for 1 hr
  4. filtrationAn insoluble portion was filtered through celite
  5. washwashed with ethyl acetate and water
  6. customThe organic layer of the filtrate was separated
  7. washwashed with water and brine in this order
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under a reduced pressure
  10. customto give a residue
  11. filtrationCrystals was filtered off
  12. customdried under aeration

Sources & evidence

ORD record
ord-89b19bd8f27d4280b78b2d296486b9b6
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

Loading…