Hydrochloric Acid → HCID 59363670, compound

HRID 1094756Notes

Reaction equation

HRID 1094756 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[C:5]([O:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.[O-:14][Mn](=O)(=O)=O.[K+].[OH-].[K+].Cl>O.CO>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:14])=[O:9])[C:5]([O:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 593636466-Methyl-3-propoxy-2-pyridinemethanol

Product 1

HCID 59363670HCID 59363670, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a 500 ml round-bottom flask [6-methyl-3-(propyloxy)-2-pyridinyl]methanol D14 (3.50 g) was suspended in water (16 ml) and KMnO4 (6.10 g, 38.60 mmol) and KOH (1 M aqueous solution, 19 ml, 19 mmol) were added. The mixture was stirred at room temperature for 2 hours. The pH was adjusted to pH=4 by addition of a 1 M aqueous HCl solution and then MeOH (100 ml) was added. The solid was filtered off, volatiles were removed under reduced pressure and the aqueous phase was extracted twice with DCM. The collected organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford the title compound D16 (2 g). MS: (ES/+) m/z: 196 (M+1). C10H13NO2 requires 195. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 12.96 (bs, 1 H), 7.49 (d, 1 H), 7.31 (d, 1 H), 3.98 (t, 2H), 2.40 (s, 3 H), 1.60-1.80 (m, 2 H), 0.96 (t, 3 H).

Workup

  1. filtrationThe solid was filtered off
  2. customvolatiles were removed under reduced pressure
  3. extractionthe aqueous phase was extracted twice with DCM
  4. washThe collected organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a660c7db2ea0416884d4ef7f722078a2
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Reaction notes

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