Acetic Acid → HCID 21278591, compound

HRID 981819Notes

Reaction equation

HRID 981819 reaction equation
Cl[C:2]1[CH:7]=[C:6](CC(O)CO)[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([NH:16][CH2:17][CH:18]([OH:21])[CH2:19][OH:20])[C:3]=1N.[C:23]([OH:26])(=O)[CH3:24].C(O)=O.[OH2:30].C([N:33]([CH2:36]C)CC)C>[Pd]>[OH:21][CH:18]([CH2:19][OH:20])[CH2:17][NH:16][C:4]1[CH:3]=[CH:2][CH:7]=[C:6]([NH:33][CH2:36][CH:23]([OH:26])[CH2:24][OH:30])[C:5]=1[N+:13]([O-:15])=[O:14]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 284Formic AcidHCID 962WaterHCID 8471TriethylamineHCID 86744611HCID 86744611, compound

Product 1

HCID 21278591HCID 21278591, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

240 mg of palladium at a concentration of 10% on calcium carbonate are added to 0.012 mole (4 g) of 4-chloro-2-(β,γ-dihydroxypropyl)amino-6-(β,γ-dihydroxypropyl)-aminonitrobenzene in 8.6 ml of triethylamine. 0.8 ml of acetic acid and 1.65 ml of formic acid are then added dropwise. The reaction mixture is heated under reflux for 7 hours. 10 ml of water are added. The reaction mixture diluted in this manner is filtered hot to remove the catalyst. The filtrate is evaporated to dryness under vacuum in the presence of absolute ethanol. The residue is dissolved in the minimum quantity of water. The expected product is extracted with ethyl acetate. The ethyl acetate phases are evaporated to dryness, after drying over sodium sulphate. After a small quantity of water has been added to the oil obtained, the expected product precipitates. Recrystallized from ethyl acetate, it melts at 138° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 7 hours
  3. additionThe reaction mixture diluted in this manner
  4. filtrationis filtered hot
  5. customto remove the catalyst
  6. customThe filtrate is evaporated to dryness under vacuum in the presence of absolute ethanol
  7. dissolutionThe residue is dissolved in the minimum quantity of water
  8. extractionThe expected product is extracted with ethyl acetate
  9. customThe ethyl acetate phases are evaporated to dryness
  10. dry with materialafter drying over sodium sulphate
  11. additionAfter a small quantity of water has been added to the oil
  12. customobtained
  13. customthe expected product precipitates
  14. customRecrystallized from ethyl acetate, it melts at 138° C.

Sources & evidence

ORD record
ord-f48dbbf9a2b34e658861653d712680d9
Source dataset
uspto-grants-1991_02
Patent number
US04992586

Reaction notes

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