Isopropanol → HCID 22145851, compound

HRID 1994348Notes

Reaction equation

HRID 1994348 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH:7]1([O:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([CH2:21][OH:22])[CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[K+].C([OH:28])(C)C>O>[CH:7]1([O:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([C:21]([OH:28])=[O:22])[CH:14]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 516875Potassium Permanganate2×HCID 22145868HCID 22145868, compound

Product 1

HCID 22145851HCID 22145851, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

Solid potassium permanganate (5.87 g) is added portionwise during 30 minutes to a suspension of 4-cyclopentyloxy-2-hydroxymethyl-5-methoxypyridine (4.0 g) in water (100 mL) at 50±5° C. When the addition is complete the mixture is heated at 70±5° C. for 45 min and then cooled to room temperature. A solution of potassium hydroxide (1.95 g) in water (50 mL) is added followed by sufficient isopropanol to react with excess potassium permanganate. After stirring for 10 minutes the mixture is filtered through diatomaceous earth and the filtrate concentrated to ˜70 mL. The solution is acidified to pH 2 with concentrated aqueous hydrochloric acid and extracted with chloroform. After drying (MgSO4) the extracts are evaporated to give 4-cyclopentyloxy-5-methoxypyridine-2-carboxylic acid (2.5 g) as a white solid, m.p. 184-5° C. [1Hnmr in D6-DMSO shifts relative to Me4Si:— 1.55-1.79, 6H, m; 1.95, 2H, m; 3.92, 3H, s; 5.00, 1H, m; 7.59, 1H, s; 8.24, 1H, s.].

Workup

  1. additionWhen the addition
  2. temperaturecooled to room temperature
  3. filtrationis filtered through diatomaceous earth
  4. concentrationthe filtrate concentrated to ˜70 mL
  5. extractionextracted with chloroform
  6. dry with materialAfter drying (MgSO4) the extracts
  7. customare evaporated

Sources & evidence

ORD record
ord-8ddc1c05fb794101b91080fe49caee85
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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