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87129-71-3

87129-71-3 Structure

87129-71-3 Structure
IdentificationBack Directory
[Name]

Arnolol
[CAS]

87129-71-3
[Synonyms]

Arnolol
3-Amino-1-[4-(2-methoxyethyl)phenoxy]-3-methylbutan-2-ol
1-[4-(2-methoxyethyl)-phenoxy]-3-amino-3-methyl-butan-2-ol
2-Butanol, 3-amino-1-[4-(2-methoxyethyl)phenoxy]-3-methyl-
[Molecular Formula]

C14H23NO3
[MDL Number]

MFCD00868795
[MOL File]

87129-71-3.mol
[Molecular Weight]

253.34
Hazard InformationBack Directory
[Originator]

Arnolol,ZYF Pharm Chemical
[Uses]

Arnolol is a beta blocker with a pressure-lowering action[1].
[Manufacturing Process]

2 methods of producing of 1-[4-(2-methoxyethyl)-phenoxy]-3-amino-3- methyl-butan-2-ol:
1). 19.0 g of 1-[4-(2-methoxyethyl)phenoxy]-3-nitro-3-methylbutan-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 4.0 g of palladiumon- charcoal (10% Pd). After the mixture has been filtered and the solvent has been evaporated off, the residue is rendered alkaline with 2 N NaOH and the mixture is extracted with CH2Cl2. The organic phase is washed with water and dried with Na2SO4 to give, after evaporation, 15.0 g of the 1-[4-(2- methoxyethyl)phenoxy]-3-amino-3-methylbutan-2-ol, melting point 120°- 122°C (dec.).
2). 18.3 g of zinc dust are gradually added to 20.0 g of 1-[4-(2-methoxyethyl) phenoxy]-3-nitro-3-methylbutan-2-ol in 400 ml of ethanol and 60 ml of concentrated hydrochloric acid at 50°-60°C. The mixture is stirred at this temperature for 1 h and filtered and the solvent is evaporated off. After 200 ml of 40% strength NaOH have been added, the product is extracted with methylene chloride. Solvent is distilled and the 1-[4-(2-methoxyethyl) phenoxy]-3-amino-3-methylbutan-2-ol is produced, melting point 120°-122°C (dec.).
[Therapeutic Function]

Beta-adrenergic blocker (ophthalmic)
[References]

[1] P Ashton, et al. The effect of chlorhexidine acetate on the corneal penetration of sorbitol from an arnolol formulation in the albino rabbit. J Ocul Pharmacol. 1990 Spring;6(1):37-42. DOI:10.1089/jop.1990.6.37
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