1-Naphthol → Propranolol

HRID 2198835Notes

Reaction equation

HRID 2198835 reaction equation
[CH:1]([N:4]1[CH2:7][CH:6]([OH:8])[CH2:5]1)([CH3:3])[CH3:2].[C:9]1([OH:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.[OH-].[K+]>>[C:9]1([O:19][CH2:5][CH:6]([OH:8])[CH2:7][NH:4][CH:1]([CH3:2])[CH3:3])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 70051-NaphtholHCID 14797Potassium HydroxideHCID 5446771-(Propan-2-yl)azetidin-3-ol

Product 1

HCID 4946PropranololYield 76%

Conditions

Temperature
160 °C

Procedure

To a mixture of 11.5 parts of 1-(iso-propyl)-3-azetidinol and 15.8 parts of α-naphthol 0.2 part of potassium hydroxide was added, and the mixture was heated under nitrogen gas at 160° C. for 20 hours. The reaction mixture was cooled and then extracted with ether. The ether extract was washed with 2 N-NaOH aqueous solution and then with water. The liquor was dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was recrystallized from cyclohexane or subjected to distillation under reduced pressure. As a result, 19.6 parts of 1-(α-naphthoxy)-3-(isopropylamino)-2-propanol having a melting point of 94°-96° C. and a boiling point of 158°-159° C. under 2.5 mm Hg were obtained. The yield was 76%. The results of infra-red spectrum analysis of the product are as follows:

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with 2 N-NaOH aqueous solution
  6. dry with materialThe liquor was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized from cyclohexane
  9. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-229c6579ff374eec9dd9b6ee84c35fdb
Source dataset
uspto-grants-1982_11
Patent number
US04360464

Reaction notes

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