Ethanol → 4-Pyrimidinecarboxylic acid

HRID 1259485Notes

Reaction equation

HRID 1259485 reaction equation
[CH3:1][C:2]1C=C[N:5]=[CH:4][N:3]=1.[Mn]([O-])(=O)(=O)=O.[K+].[OH-:14].[K+].[CH2:16]([OH:18])[CH3:17]>O>[N:3]1[CH:2]=[CH:1][C:17]([C:16]([OH:14])=[O:18])=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 189224-MethylpyrimidineHCID 516875Potassium Permanganate

Product 1

HCID 1693064-Pyrimidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

4-Methylpyrimidine (1.00 g, 10.6 mmol) was diluted in water (90 mL). Potassium permanganate (4.20 g, 26.5 mmol) and potassium hydroxide (4.20 g, 74.8 mmol) were added, and the mixture was heated at 75° C. for 1.5 h. Ethanol was added dropwise, and the precipitate was removed by filtration through Celite. The filtrate was concentrated under reduced pressure, diluted in water, and treated with a concentrated HCl solution until acidic. The title compound precipitated as a fine powder, which was collected by vacuum filtration and dried in a vacuum oven (770 mg, 58%): 1H NMR (DMSO-d6) δ: 13.92 (1H, br s), 9.35 (1H, d), 9.05 (1H, d), 7.99 (1H, dd).

Workup

  1. customthe precipitate was removed by filtration through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additiondiluted in water
  4. additiontreated with a concentrated HCl solution until acidic
  5. customThe title compound precipitated as a fine powder, which
  6. filtrationwas collected by vacuum filtration
  7. customdried in a vacuum oven (770 mg, 58%)

Sources & evidence

ORD record
ord-493d4a8103e64f5db7293fad8bb6ce4c
Source dataset
uspto-grants-2013_06
Patent number
US08466283B2

Reaction notes

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