Sodium Hydroxide → 5-[1-(3-Ethoxy-4-methoxy-phenyl)-propenyl]-2-methoxy-phenylamine

HRID 2378264Notes

Reaction equation

HRID 2378264 reaction equation
O.O.Cl[Sn]Cl.[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([N+:28]([O-])=O)[CH:21]=2)=[CH:18][CH3:19])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH3:7].[OH-].[Na+]>C(O)C.C(OCC)(=O)C>[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([NH2:28])[CH:21]=2)=[CH:18][CH3:19])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH3:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 692050534-[1-(3-Ethoxy-4-methoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene

Product 1

HCID 692047575-[1-(3-Ethoxy-4-methoxy-phenyl)-propenyl]-2-methoxy-phenylamineYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

SnCl2.2H2O (3.98 g, 17.6 mmol) was added to a stirred suspension of (E/Z) 4-[1-(3-ethoxy-4-methoxy-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-ethoxy-4-methoxy-phenyl) -propenyl]-2-methoxy-phenylamine as a solid (0.73 g, 73% yield): mp, 108-110° C.; 1H NMR (CDCl3) δ 1.39-1.46 (m, 6H, 2CH3), 1.72-1.77 (m, 6H, 2CH3), 3.71-3.75 (bp, 4H, 2NH2), 3.83-3.90 (m, 12H, 4OCH3), 3.99-4.09 (m, 4H, 2CH2), 5.97-6.05 (m, 2H, 2CH), 6.54-6.61 (m, 12H, Ar); 13C NMR (CDCl3) δ 14.79, 15.67, 15.72, 55.45, 55.52, 55.90, 55.95, 64.21, 64.26, 109.90, 109.95, 110.97, 111.01, 112.13, 114.11, 114.80, 116.83, 117.51, 119.89, 120.35, 121.81, 121.98, 122.44, 132.86, 132.93, 135.52, 135.57, 136.28, 136.49, 141.93, 142.02, 146.25, 146.53, 147.75, 148.02, 148.34; Anal. Calcd for C19H23NO3: C, 73.82; H, 7.40; N, 4.47. Found: C, 72.57; H, 7.47; N, 4.40.

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-33594a011eb04649ab8cff04fa368f66
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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