Potassium Hydroxide → Pirbuterol

HRID 1285338Notes

Reaction equation

HRID 1285338 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH:7]([OH:17])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH2:15][OH:16])[N:9]=1)([CH3:4])[CH3:3].Cl.Cl.[OH-].[K+]>CO>[CH3:4][C:2]([NH:5][CH2:6][CH:7]([OH:17])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH2:15][OH:16])[N:9]=1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68658Pirbuterol hydrochloride

Product 1

HCID 4845Pirbuterol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under nitrogen, pirbuterol dihydrochloride (3.0 g., 0.0096 mol) was dissolved in 10 ml. CH3OH. KOH (85%, 1.3 g., 0.0197 mol) in 30 ml. of CH3OH was added dropwise over 10 minutes. After stirring 30 minutes, precipitated KCl (1.25 g.) was removed by filtration and the mother liquor evaporated to a white foam, 2.56 g. The latter was taken up in 20 ml. 1:1 acetone:CH3OH and allowed to stand 18 hours. Additional KCl (0.09 g.) was recovered by filtration and the mother liquor evaporated in vacuo to yield title product, dried under high vacuum, 2.35 g.

Workup

  1. customprecipitated KCl (1.25 g.)
  2. customwas removed by filtration
  3. customthe mother liquor evaporated to a white foam, 2.56 g
  4. waitto stand 18 hours
  5. filtrationAdditional KCl (0.09 g.) was recovered by filtration
  6. customthe mother liquor evaporated in vacuo

Sources & evidence

ORD record
ord-e1226f4c39b44f59814141624f46007b
Source dataset
uspto-grants-1986_01
Patent number
US04567179

Reaction notes

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