Hydrochloric Acid → 1-(1H-Indazol-4-yloxy)-3-((2-(2,6-xylidino)ethyl)amino)-2-propanol

HRID 1633256Notes

Reaction equation

HRID 1633256 reaction equation
C([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[C:14]2[O:17][CH2:18][CH:19]([OH:33])[CH2:20][NH:21][CH2:22][CH2:23][NH:24][C:25]2[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:32])=[N:9]1)C1C=CC=CC=1.Cl>[Pd].CO>[NH:9]1[C:10]2[C:15](=[C:14]([O:17][CH2:18][CH:19]([OH:33])[CH2:20][NH:21][CH2:22][CH2:23][NH:24][C:25]3[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][C:26]=3[CH3:32])[CH:13]=[CH:12][CH:11]=2)[CH:16]=[N:8]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13131637HCID 13131637, compound

Product 1

HCID 30477891-(1H-Indazol-4-yloxy)-3-((2-(2,6-xylidino)ethyl)amino)-2-propanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.8 g. 1-(2-Benzylindazol-4-yloxy)-3-[2-(2,6-dimethylphenylamino)-ethylamino]-propan-2-ol in 100 ml. methanol and 10 ml. concentrated hydrochloric acid are hydrogenated over 0.9 g. of 10% palladium-charcoal. After suction filtration, the filtrate is evaporated, the residue is dissolved in water, rendered alkaline with aqueous sodium hydroxide solution and extracted with methylene chloride. The organic phase is evaporated and the residue is triturated with diethyl ether and filtered off with suction. After recrystallization from ethyl acetate, the desired compound is obtained in a yield of 3.9 g. (72% of theory); m.p. 127°-128° C.

Workup

  1. filtrationAfter suction filtration
  2. customthe filtrate is evaporated
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with methylene chloride
  5. customThe organic phase is evaporated
  6. customthe residue is triturated with diethyl ether
  7. filtrationfiltered off with suction
  8. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5d1122d3314148e6ac0ee2617c307a88
Source dataset
uspto-grants-1984_10
Patent number
US04479962

Reaction notes

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