Hydrochloric Acid → HCID 20369780, compound

HRID 1283222Notes

Reaction equation

HRID 1283222 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][O:8][C:9]2[CH:22]=[CH:21][C:20]3[C:19](=[O:23])[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:24][CH2:25][CH2:26][N:27]5C(=O)C6=CC=CC=C6C5=O)[CH:17]=4)[C:12](=[O:38])[C:11]=3[CH:10]=2)C(=O)C2=CC=CC=C12.O.NN.Cl>CO.O>[NH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:22]=[CH:21][C:20]2[C:19](=[O:23])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:24][CH2:25][CH2:26][NH2:27])[CH:17]=3)[C:12](=[O:38])[C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 20369767HCID 20369767, compound

Product 1

HCID 20369780HCID 20369780, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 17.4 g (0.03 mole) of the intermediate 2,6-bis-(2-phthalimidoethoxy)anthraquinone, prepared in (A) above, 200 ml. of methanol, and 3.6 g. (0.06 mole) of hydrazine hydrate (85% is heated to reflux for 4 hours. Water (100 ml.) is added and the methanol boiled out of the mixture. Then, 75 ml. of 37% hydrochloric acid is added and the resulting mixture heated to reflux for another hour. The mixture is allowed to cool, then chilled at 0°C., and the precipitate of phthalhydrazide removed by filtration with suction. The filtrate is evaporated to dryness, made alkaline with 10% sodium hydroxide, and the base is extracted into chloroform. The chloroform layer is washed with water, dried with anhydrous magnesium sulfate, filtered, and the chloroform evaporated. The 2,6-bis-(2-aminoethoxy)anthraquinone base is converted to the dihydrochloride salt as described in Example 1, and recrystallized from a solvent or solvent mixture such as isopropanol, ethanol/ether, or butanone/methanol. In a similar manner, 2,7-bis(2-aminoethoxy)anthraquinone can be prepared from 2,7-bis(2-chloroethoxy)anthraquinone.

Workup

  1. temperatureto reflux for 4 hours
  2. temperaturethe resulting mixture heated
  3. temperatureto reflux for another hour
  4. temperatureto cool
  5. customthe precipitate of phthalhydrazide removed by filtration with suction
  6. customThe filtrate is evaporated to dryness
  7. extractionthe base is extracted into chloroform
  8. washThe chloroform layer is washed with water
  9. dry with materialdried with anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customthe chloroform evaporated
  12. customrecrystallized from a solvent or solvent mixture such as isopropanol, ethanol/ether, or butanone/methanol
  13. customIn a similar manner, 2,7-bis(2-aminoethoxy)anthraquinone can be prepared from 2,7-bis(2-chloroethoxy)anthraquinone

Sources & evidence

ORD record
ord-d9ab8f09e51c458fb0241ad8651a1d29
Source dataset
uspto-grants-1976_08
Patent number
US03974186

Reaction notes

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