HCID 13186853, compound → Arnolol

HRID 1607371Notes

Reaction equation

HRID 1607371 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][CH:11]([OH:18])[C:12]([N+:15]([O-])=O)([CH3:14])[CH3:13])=[CH:7][CH:6]=1>C(O)C.C(O)(=O)C.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][CH:11]([OH:18])[C:12]([NH2:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=1

Participants

5

Reactant 1

HCID 13186853HCID 13186853, compound

Product 1

HCID 65653Arnolol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

19 g of 1-[4-(2-methoxyethyl)-phenoxy]-3-nitro-3-methyl-butan-2-ol are hydrogenated at 60° C. and under a pressure of 6 bar in a mixture of 250 ml of ethanol and 50 ml of glacial acetic acid in the presence of 4 g of palladium-on-charcoal (10% Pd). After the mixture has been filtered and the solvent has been evaporated off, the residue is rendered alkaline with 2N NaOH and the mixture is extracted with CH2Cl2. The organic phase is washed with water and dried with Na2SO4 to give, after evaporation, 15 g of the amine, which is converted into the hydrochloride with ethanol hydrochloric acid. Melting point: 120°-122° C. (ethyl acetate).

Workup

  1. filtrationAfter the mixture has been filtered
  2. customthe solvent has been evaporated off
  3. extractionthe mixture is extracted with CH2Cl2
  4. washThe organic phase is washed with water
  5. dry with materialdried with Na2SO4
  6. customto give
  7. customafter evaporation, 15 g of the amine, which

Sources & evidence

ORD record
ord-0427ed68a2ca4a3dabafe90c034d3c4f
Source dataset
uspto-grants-1989_09
Patent number
US04864061

Reaction notes

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