Sodium Sulfide → (E)-3-(5-Amino-2-methoxy-phenyl)-N-methyl-acrylamide

HRID 47446

Reaction equation

HRID 47446 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:16][CH3:17])=[C:8](/[CH:10]=[CH:11]/[C:12]([NH:14][CH3:15])=[O:13])[CH:9]=1)([O-])=O.[S-2].[Na+].[Na+]>O1CCOCC1.O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:16][CH3:17])=[C:8](/[CH:10]=[CH:11]/[C:12]([NH:14][CH3:15])=[O:13])[CH:9]=1

Participants

4

Reactant 2

HCID 14804Sodium SulfideHCID 22745125(E)-3-(5-Nitro-2-methoxy-phenyl)-N-methyl-acrylamide

Product 1

HCID 22745135(E)-3-(5-Amino-2-methoxy-phenyl)-N-methyl-acrylamideYield 76.4%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

(E)-3-(5-Nitro-2-methoxy-phenyl)-N-methyl-acrylamide (0.75 g) and sodium sulphide (1.0 g) were combined in 1,4-dioxan/water (1:1, 20 ml) and warmed at 80° C. for 3 h. Solvent was removed at reduced pressure, the residue extracted with 10% methanol/dichloromethane and the extract filtered. The filtrate was evaporated to dryness and the residue column chromatographed (silica gel, 5% methanol:dichloromethane) to give the title compound (0.50 g). 1 H NMR δ: 2.68 (3H, d, J=0.4.8Hz), 3.71 (3H, s), 6.44 (1H, d, J=15.9 Hz), 6.60 (1H, dd, J=2.8 9.2 Hz), 6.73 (1H, d, J=2.8 Hz), 6.78 (1H, d, J=9.2 Hz), 7.57 (1H, d, J=15.9 Hz), 8.00 (1H, m).

Workup

  1. customSolvent was removed at reduced pressure
  2. extractionthe residue extracted with 10% methanol/dichloromethane
  3. filtrationthe extract filtered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue column chromatographed (silica gel, 5% methanol:dichloromethane)

Sources & evidence

ORD record
ord-9388a508099842338558fe8c87ef9d8a
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Linked notes

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