Water → HCID 19751972, compound

HRID 1087685Notes

Reaction equation

HRID 1087685 reaction equation
[H][H].O.[C:4]([NH:7][C:8]1[C:9]([O:20][CH3:21])=[C:10]([N+:17]([O-])=O)[C:11]([O:15][CH3:16])=[C:12]([Cl:14])[CH:13]=1)(=[O:6])[CH3:5]>[Fe].C(O)(=O)C>[C:4]([NH:7][C:8]1[C:9]([O:20][CH3:21])=[C:10]([NH2:17])[C:11]([O:15][CH3:16])=[C:12]([Cl:14])[CH:13]=1)(=[O:6])[CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 19751955HCID 19751955, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19751972HCID 19751972, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

253 g of powdered iron which had been reduced with hydrogen were added to 760 ml of water containing 13 ml of acetic acid and which had been previously heated to 80° C., and then 0.46 mole (126.5 g) of 5-acetamido-2,4-dimethoxy-3-nitrochlorobenzene prepared in the previous step was added gradually with stirring. Upon completion of the additions, the reaction mixture was maintained in a boiling water bath for 15 minutes. After cooling, the reaction mixture was centrifuged. The iron slurries, after being separated from the liquid phase, were extracted with ethyl acetate. The ethyl acetate phase which was washed with water and then dried over sodium sulphate was diluted with 100 ml of a 7N hydrochloric acid solution in absolute ethanol. The expected product, which precipitated in the form of hydrochloride was thoroughly drained. It was dissolved in the minimum amount of water. After neutralization, the expected product precipitated. Recrystallized from alcohol, it melted at 113° C.

Workup

  1. additionwas added gradually
  2. temperatureUpon completion of the additions, the reaction mixture was maintained in a boiling water bath for 15 minutes
  3. temperatureAfter cooling
  4. customThe iron slurries, after being separated from the liquid phase
  5. extractionwere extracted with ethyl acetate
  6. washThe ethyl acetate phase which was washed with water
  7. dry with materialdried over sodium sulphate
  8. additionwas diluted with 100 ml of a 7N hydrochloric acid solution in absolute ethanol
  9. customThe expected product, which precipitated in the form of hydrochloride
  10. dissolutionIt was dissolved in the minimum amount of water
  11. customAfter neutralization, the expected product precipitated
  12. customRecrystallized from alcohol, it melted at 113° C.

Sources & evidence

ORD record
ord-f57bd01ca2a04b8fb02265837eb6e99f
Source dataset
uspto-grants-1990_10
Patent number
US04960432

Reaction notes

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