Methanesulfonic Acid → Isopropanol

HRID 1381665Notes

Reaction equation

HRID 1381665 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[O:15])[C:8](=[N:13]O)[C:9](=[O:12])[CH2:10][CH3:11])=[CH:3][CH:2]=1.CS(O)(=O)=O>C(O)=O.CO.[Zn]>[CH:9]([OH:12])([CH3:10])[CH3:8].[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([OH:15])[CH:8]([NH2:13])[C:9](=[O:12])[CH2:10][CH3:11])=[CH:3][CH:2]=1

Participants

7

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178459333HCID 178459333, compound

Product 2

HCID 3776IsopropanolYield 1,006.6%HCID 14350447HCID 14350447, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 284Formic AcidSolvent2×HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

In 37.8 kg of 88% formic acid was dissolved 7.5 kg (91% pure, 36.37 mole) of 1-(4-pyridyl)-1,3-diketo-2-oximinopentane and 7.0 kg of methanesulfonic acid. The resulting solution was slowly added to a slurry of 8.3 kg of zinc powder in 35.7 kg of formic acid. The reaction temperature was kept at about 60° C. by proper cooling and slow addition. The mixture was allowed to stir at 55° C. for 2 hours and then cooled to 20° C. The solid zinc formate was filtered off. To the formic acid filtrate was added 3.6 kg of methanesulfonic acid. The formic acid was removed at the reduced pressure (40 mm Hg) and 70° C. To the residue was added a solution of 5.9 kg of methanol and 53.3 kg of isopropanol and stirred at 20° C. for 4 hours. Solid material was collected by centrifugation, washed with 12.5 kg of 10% methanol in isopropanol giving 11.0 kg, 87% yield, of the title compound as dimethanesulfonate salt after drying.

Workup

  1. customwas kept at about 60° C.
  2. temperatureby proper cooling
  3. additionslow addition
  4. temperaturecooled to 20° C
  5. filtrationThe solid zinc formate was filtered off
  6. additionTo the formic acid filtrate was added 3.6 kg of methanesulfonic acid
  7. customThe formic acid was removed at the reduced pressure (40 mm Hg) and 70° C
  8. additionTo the residue was added a solution of 5.9 kg of methanol and 53.3 kg of isopropanol
  9. stirringstirred at 20° C. for 4 hours
  10. customSolid material was collected by centrifugation

Sources & evidence

ORD record
ord-416c4d346a1e4aa7b3e5387ac1e259a5
Source dataset
uspto-grants-1989_02
Patent number
US04803278

Reaction notes

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