Ammonium Chloride → HCID 9925276, compound

HRID 229659Notes

Reaction equation

HRID 229659 reaction equation
[Cl-].[NH4+].[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12](=[O:32])[N:13]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:16]=1)#[N:4]>CC(O)C.O.[Fe]>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12](=[O:32])[N:13]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=2)[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:16]=1)#[N:4]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 10157448HCID 10157448, compound

Product 1

HCID 9925276HCID 9925276, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Iron powder (180 mg) and 342 mg of ammonium chloride were added to a solution of 317 mg of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-(3-nitrophenyl)-1,2-dihydropyridin-2-one in a mixture of 10 ml of 2-propanol and 5 ml of water followed by refluxing for 4 hours. The reaction mixture was concentrated, partitioned in ethyl acetate-water, the organic layer was washed with water, dried and concentrated and the residue was purified by a silica gel column chromatography (ethyl acetate/hexane system) to give 235 mg of the title compound as a pale yellow solid.

Workup

  1. temperatureby refluxing for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned in ethyl acetate-water
  4. washthe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by a silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-a6470c3107434c1c973c6230cfcbb821
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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