Sodium Hydroxide → 5-[1-(3,5-Dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamine

HRID 2378266Notes

Reaction equation

HRID 2378266 reaction equation
O.O.Cl[Sn]Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([N+:27]([O-])=O)[CH:20]=2)=[CH:17][CH3:18])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1.[OH-].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([NH2:27])[CH:20]=2)=[CH:17][CH3:18])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 692040644-[1-(3,5-Dimethoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene

Product 1

HCID 692036045-[1-(3,5-Dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamineYield 66.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

SnCl2.2H2O (5.20 g, 23.0 mmol) was added to a stirred solution of (E/Z) 4-[1-(3,5-dimethoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene (1.10 g, 3.2 mmol) in ethanol (200 proof, 20 mL) and ethyl acetate (10 mL). The reaction mixture was heated at 70° C. for 1 h. The solution was cooled down to room temperature, poured into ice water (100 mL), and basified with 10 N NaOH (20 mL) to pH ˜12. The aqueous layer was extracted with ethyl acetate (5×35 mL). The combined organic layers were washed with water (60 mL), brine (50 mL) and dried (MgSO4). Removal of solvent and chromatography (Silica Gel) gave a mixture of (E/Z) 5-[1-(3,5-dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamine as an oil (0.64 g, 51% yield): 1H NMR (CDCl3) δ 1.70-1.78 (2d, J=7.0 Hz, 6H, 2CH3), 3.74-3.87 (4s+m, 22H, 6OCH3+2NH2), 6.02-6.10 (m, 2H, 2CH), 6.33-6.79 (m, 12H, Ar); 13C NMR (CDCl3) δ 15.60, 15.73, 55.30, 55.45, 55.52, 98.70, 98.92, 105.72, 107.99, 109.95, 109.99, 113.91, 116.77, 117.30, 120.32, 122.05, 123.83, 132.49, 135.56, 135.61, 142.09, 142.33, 142.50, 145.66, 146.32, 146.56, 160.36, 160.51; Anal. Calcd for C18H21NO3: C, 72.22; H, 7.07; N, 4.68. Found: C, 71.94; H, 7.37; N, 4.54.

Workup

  1. temperatureThe solution was cooled down to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (5×35 mL)
  3. washThe combined organic layers were washed with water (60 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customRemoval of solvent and chromatography (Silica Gel)
  6. customgave

Sources & evidence

ORD record
ord-f74be3d125824eb18db6da8bb9946212
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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