Isopropanol → HCID 22145750, compound

HRID 1994359Notes

Reaction equation

HRID 1994359 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH:7]1([O:12][C:13]2[C:18]([O:19][CH:20]([F:22])[F:21])=[CH:17][N:16]=[C:15]([CH2:23][OH:24])[CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[K+].C([OH:30])(C)C>O>[CH:7]1([O:12][C:13]2[C:18]([O:19][CH:20]([F:21])[F:22])=[CH:17][N:16]=[C:15]([C:23]([OH:30])=[O:24])[CH:14]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 516875Potassium Permanganate2×HCID 22145875HCID 22145875, compound

Product 1

HCID 22145750HCID 22145750, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

Solid potassium permanganate (306 mg) is added portionwise to a stirred suspension of 4-cyclopentyloxy-5-difluoromethoxy-2-hydroxymethylpyridine (250 mg) in water (10 mL) while heating at 50±5° C. The resulting mixture is heated for 1.5 hours at this temperature, then at 70° C. for minutes. A solution of potassium hydroxide (150 mg) in water (1 mL) is added followed by the addition of isopropanol until the excess potassium permanganate is consumed. After 15 minutes, the mixture is cooled and filtered through a pad of diatomaceous earth and the filtrate adjusted to pH 5 with glacial acetic acid. The white precipitate is collected, washed with water and dried in vacuo to give 4-cyclopentyloxy-5-difluoromethoxypyridine-2-carboxylic acid (240 mg) as a white solid, m.p. 215-6° C. decomp. [Elemental analysis: —C, 52.57; H, 4.67; N, 5.18%. calculated: —52.75; H, 4.80; N, 5.13%].

Workup

  1. temperatureThe resulting mixture is heated for 1.5 hours at this temperature
  2. waitat 70° C. for minutes
  3. customis consumed
  4. temperaturethe mixture is cooled
  5. filtrationfiltered through a pad of diatomaceous earth
  6. customThe white precipitate is collected
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a352af3e300e42a98e576639092855fe
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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