Water → HCID 10089770, compound

HRID 1455722Notes

Reaction equation

HRID 1455722 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:25])[CH:11]=[CH:12][C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)=[CH:5][C:4]=1[N+:26]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].O.C(OCC)(=O)C>CC(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:25])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)=[CH:5][C:4]=1[NH2:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 68952183HCID 68952183, compound

Product 1

HCID 10089770HCID 10089770, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of N-(4-methoxy-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl) -2-propenamide (Example 3) (1.3 mmol) in acetone/water (10:5) was heated to 50° C. After 30 minutes, sodium hydrosulfite (Na2S2O4) (26.3 mmol) was added slowly. The resulting mixture was heated at reflux for one hour and then cooled to room temperature. Water was added to the cooled reaction mixture. The product was isolated by extraction with ethyl acetate. The organic layer washed with 10% aqueous NaHCO3 and then dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The crude product thereby obtained was recrystallized from 2-propanol to yield the title compound, melting point 202-204° C., in 32% yield.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for one hour
  3. washThe organic layer washed with 10% aqueous NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customThe crude product thereby obtained
  7. customwas recrystallized from 2-propanol

Sources & evidence

ORD record
ord-76f6f2e4ca014001bedbaae05648851c
Source dataset
uspto-grants-2009_01
Patent number
US07482488B2

Reaction notes

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