Acetone → HCID 68992758, compound

HRID 1908258Notes

Reaction equation

HRID 1908258 reaction equation
[N+:1]([CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1)[OH:6])([O-])=O.CC(C)=O.[NH4+].[Cl-]>[Zn].O>[NH2:1][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1)[OH:6]

Participants

6

Reactant 3

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 68630899HCID 68630899, compound

Product 1

HCID 68992758HCID 68992758, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

To a solution of consisting of 2-nitro-1-(4-pyridin-2-yl-phenyl)-ethanol (275 mg, 1.1 mmol) and acetone (5 mL) were added NH4Cl (900 mg, 16.9 mmol), Zn dust (1.10 g, 16.9 mmol), and water (1 mL). The reaction mixture was stirred for 2 h at rt and then filtered. The filtrate was washed with saturated NaHCO3 and extracted with EtOAc. The organic layer was dried (Na2SO4) and concentrated. The crude residue was purified (FCC) to give the title compound (45 mg, 19%).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with saturated NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-00e4c1fe56e7406a9a876eb5d3a81fa6
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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