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

HRID 2378268Notes

Reaction equation

HRID 2378268 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N+:22]([O-])=O)[CH:15]=2)=[CH2:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C.C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([NH2:22])[CH:15]=2)=[CH2:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 692049451-(3-Ethoxy-4-methoxy-phenyl)-1-(3-nitro-4-methoxy-phenyl)-ethene

Product 1

HCID 115945815-[1-(3-Ethoxy-4-methoxy-phenyl)-vinyl]-2-methoxy-phenylamineYield 48%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 1-(3-ethoxy-4-methoxy-phenyl)-1-(3-nitro-4-methoxy-phenyl)-ethene (0.9 g, 2.8 mmol) in ethyl acetate (10 mL) and ethanol (20 mL) was added tin (II) chloride dihydrate (3.5 g, 15.4 mmol). The mixture was heated at 70° C. for 1 hr. The mixture was poured into ice water (100 mL) and basified with 10 N sodium hydroxide to pH=10. The mixture was extracted with ethyl acetate (5×35 mL). The combined organic layers were washed water (60 mL), brine (60 mL) and dried (MgSO4). Removal of solvent and chromatography (silica gel) gave 5-[1-(3-ethoxy-4-methoxy-phenyl) -vinyl]-2-methoxy-phenylamine as a solid (0.4 g, 48% yield): mp 91-93° C.; 1H NMR (CDCl3) δ 1.43 (t, J=7.1 Hz, 3H, CH3), 3.75 (b, 2H, NH2), 3.86 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 4.06 (q, J=7.1 Hz, 2H, OCH2), 5.28 (d, J=6.5 Hz, 2H, CH2), 6.91-6.72 (m, 6H, CH); 13C NMR (CDCl3) δ 14.76, 55.50, 55.94, 64.26, 109.85, 110.91, 111.53, 113.12, 115.03, 118.67, 120.92, 134.59, 134.73, 135.58, 147.14, 147.69, 148.97, 149.59; Anal. Calcd for C18H21NO3: C, 72.22; H, 7.07; N, 4.68. Found: C, 72.16; H, 7.10; N, 4.74.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (5×35 mL)
  2. washThe combined organic layers were washed water (60 mL), brine (60 mL)
  3. dry with materialdried (MgSO4)
  4. customRemoval of solvent and chromatography (silica gel)

Sources & evidence

ORD record
ord-14198930d0c24774875fd960d3951e6c
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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