Acetone → HCID 43165626, compound

HRID 1428820Notes

Reaction equation

HRID 1428820 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[CH3:14].CC(C)=O.[Cl-].[NH4+]>CCOC(C)=O.[Zn]>[CH3:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:2]([CH3:1])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[CH3:14]

Participants

6

Reactant 3

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 68486376HCID 68486376, compound

Product 1

HCID 43165626HCID 43165626, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Zinc dust (3.86 g, 59.1 mmol) was added to a stirred solution of 4-(2,6-dimethyl-phenoxy)-3-methyl-nitrobenzene (1.5 g, 5.9 mmol), acetone (20 mL) and saturated aqueous ammonium chloride (20 mL) at 0° C. The mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was diluted with 200 mL EtOAc and filtered through diatomaceous earth. The organic layer was washed with brine, dried with sodium sulfate and concentrated to provide the crude titled compound (0.79 g, 59%). This material was used without purification: MS (ESI): mass calcd. for C15H17NO, 227.3; m/z found, 227.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.07 (d, J=7.2 Hz, 2H), 7.01 (dd, J=8.3, 6.5 Hz, 1H), 6.60 (t, J=3.4 Hz, 1H), 6.31 (dd, J=8.5, 2.9 Hz, 1H), 6.06 (d, J=8.5 Hz, 1H), 3.36 (s, 2H), 2.34 (s, 3H), 2.11 (s, 6H).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. washThe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-60a3c4279bc04e23aec5e5e61f3c2f92
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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