Water → HCID 57535844, compound

HRID 1455723Notes

Reaction equation

HRID 1455723 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[C:18]([O:19][CH3:20])=[CH:17][C:16]([O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])=[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[C:14]([O:23][CH3:24])=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=2[O:19][CH3:20])=[CH:5][C:4]=1[NH2:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 68956743HCID 68956743, compound

Product 1

HCID 57535844HCID 57535844, compoundYield 48%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
50 °C

Procedure

A solution of N-(4-methoxy-3-nitrophenyl)-3-(2,4,6-trimethoxyphenyl) -2-propenamide (example 5) (1.3mmol) in acetone/water (10:5) was heated to 50° C. After 30 min, sodium hydrosulfite (Na2S2O4) 26.3 mmol) was added slowly. The resulting mixture was heated at reflux (50° C.) for one hour. The mixture was then cooled to room temperature and water was added. 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 92-94° C., in 48% yield.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureThe mixture was then cooled to room temperature
  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-4253afa4cd814390b4ebc302e1125bca
Source dataset
uspto-grants-2009_01
Patent number
US07482488B2

Reaction notes

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