Acetic Acid → 2-(beta-Hydroxyethoxyethyl)amino-6-(beta-hydroxyethoxyethyl)aminonitrobenzene

HRID 2291443Notes

Reaction equation

HRID 2291443 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])[C:5]([N+:15]([O-:17])=[O:16])=[C:4]([NH:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][OH:24])[CH:3]=1.C(O)(=O)C.C(O)=O.O>C(N(CC)CC)C.[Pd]>[OH:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][NH:18][C:4]1[CH:3]=[CH:2][CH:7]=[C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][OH:14])[C:5]=1[N+:15]([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 962WaterHCID 200710944-Chloro-2-(beta-hydroxyethoxyethyl)amino-6-(beta-hydroxyethoxyethyl)aminonitrobenzene

Product 1

HCID 540678772-(beta-Hydroxyethoxyethyl)amino-6-(beta-hydroxyethoxyethyl)aminonitrobenzene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

300 mg of palladium at a concentration of 10% on calcium carbonate are added to 0.015 mole (5.45 g) of 4-chloro-2-(β-hydroxyethoxyethyl)amino-6-(β-hydroxyethoxyethyl)aminonitrobenzene in 11 ml of triethylamine. 1.1 ml of acetic acid and 2.05 ml of formic acid are then run in dropwise. When the additions have been completed the reaction mixture is heated under reflux for 30 minutes. 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 and the residue is taken up with ethyl acetate. Insoluble organic salts are removed by filtration. The ethyl acetate is evaporated off to dryness. Acetonitrile and then water are added to the residue. The expected product precipitates. Recrystallized from ethyl acetate, it melts at 82° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 minutes
  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. customInsoluble organic salts are removed by filtration
  8. customThe ethyl acetate is evaporated off to dryness
  9. additionAcetonitrile and then water are added to the residue
  10. customThe expected product precipitates
  11. customRecrystallized from ethyl acetate, it melts at 82° C.

Sources & evidence

ORD record
ord-2cb439cb550d4989935b3818d9d62153
Source dataset
uspto-grants-1989_01
Patent number
US04797129

Reaction notes

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