Ammonium Chloride → HCID 57677671, compound

HRID 492725Notes

Reaction equation

HRID 492725 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.[Cl-].[NH4+].C(OCC)(=O)C.O1CCCC1>C(O)C.O.[Fe]>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:23]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 21939870Tetrahydrofuran ethyl acetateHCID 57677323HCID 57677323, compound

Product 1

HCID 57677671HCID 57677671, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Piperidine-1-carboxylic acid [6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl]amide (273 mg) was dissolved in ethanol (15 ml)-water (3 ml), and then electrolytic iron powder (275 mg) and ammonium chloride (550 mg) were added thereto, followed by heating under reflux for 30 min. The reaction mixture was cooled down to room temperature, and ethyl acetate-tetrahydrofuran (1:1) was then added thereto, followed by stirring. The reaction 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 in this order, 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 (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:1 to 1:5). Fractions containing the target compound was concentrated under a reduced pressure, and dried in vacuum to provide the titled compound (235.8 mg, 94.1%) as a pale yellow solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 30 min
  3. filtrationThe reaction 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 in this order
  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 (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:1 to 1:5)
  11. additionFractions containing the target compound
  12. concentrationwas concentrated under a reduced pressure
  13. customdried in vacuum

Sources & evidence

ORD record
ord-a679ba567a9d484ab67cf995aa290862
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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