Hydrochloric Acid → HCID 178479217, compound

HRID 365222Notes

Reaction equation

HRID 365222 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH2:39][CH2:40][NH:41][CH2:42][CH2:43][OH:44])[N:11]=[C:12]3[C:21]4[C:16](=[C:17]([O:30]CC5C=CC=CC=5)[CH:18]=[CH:19][C:20]=4[O:22]CC4C=CC=CC=4)[C:15](=[O:38])[C:14]=1[C:13]=23.[ClH:45]>C(O)(=O)C.CC(O)C.[OH-].[OH-].[Pd+2]>[ClH:45].[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH2:39][CH2:40][NH:41][CH2:42][CH2:43][OH:44])[N:11]=[C:12]3[C:21]4[C:16](=[C:17]([OH:30])[CH:18]=[CH:19][C:20]=4[OH:22])[C:15](=[O:38])[C:14]=1[C:13]=23

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 13687221HCID 13687221, compound

Product 1

HCID 178479217HCID 178479217, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 9.5 g (0.016 mol) of 5-[(3-aminopropyl)amino]-2-[2-(2-hydroxyethyl)amino]ethyl]-7,10-bis(phenylmethoxy)anthra[1,9-cd[pyrazol-6(2H)-one (3) in 300 ml of acetic acid was hydrogenated over 1.7 g of 20% palladium hydroxide on carbon at atmospheric pressure and at room temperature for two hours, filtered through celite, and concentrated under vacuum. The residue was dissolved in boiling methanol. The hot solution was treated with an excess (about 0.05 mol) of hydrogen chloride in 2-propanol, and chilled overnight. The red-orange precipitate was collected, washed with 2-propanol, dried at 65° C. under vacuum for 48 hours, and allowed to equilibrate in the air overnight to afford 6.4 g (82%) of 4, containing 0.6 mole of water, mp 267°-272° C. (dec) with prior sintering.

Workup

  1. additionA mixture of 9.5 g (0.016 mol) of 5-[(3-aminopropyl)amino]-2-[2-(2-hydroxyethyl)amino]ethyl]
  2. filtrationfiltered through celite
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved
  5. temperaturechilled overnight
  6. customThe red-orange precipitate was collected
  7. washwashed with 2-propanol
  8. customdried at 65° C. under vacuum for 48 hours
  9. customto equilibrate in the air overnight

Sources & evidence

ORD record
ord-6b0a3414f2aa4384bbda54d8d7fbc0bb
Source dataset
uspto-grants-1986_08
Patent number
US04608439

Reaction notes

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