Potassium Permanganate → 7-Chloro-2,6-naphthyridine-3-carboxylic acid

HRID 468897Notes

Reaction equation

HRID 468897 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([CH2:18][OH:19])[N:14]=[CH:15]2)=[CH:10][N:9]=1>O.[OH-].[Na+]>[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:18]([OH:2])=[O:19])[N:14]=[CH:15]2)=[CH:10][N:9]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 86674969(7-Chloro-2,6-naphthyridin-3-yl)methanol

Product 1

HCID 866749707-Chloro-2,6-naphthyridine-3-carboxylic acidYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Potassium permanganate (280 mg, 1.8 mmol) was added in small portions to a slurry of (7-chloro-2,6-naphthyridin-3-yl)methanol (105 mg, 0.54 mmol) in water (2 mL). The mixture was stirred for 30 minutes at room temperature, and was then diluted with sodium hydroxide (1.0M solution in water, 5 mL) and filtered over Celite. The filtrate was acidified to a pH of ˜3 via addition of citric acid, and the resulting precipitate was collected by vacuum filtration and washed with water (2×5 mL) to afford the title compound as a white solid (55 mg, 50%). 1H NMR (400 MHz, DMSO) δ 13.40 (s, 1H), 9.54 (s, 1H), 9.51 (s, 1H), 8.82 (s, 1H), 8.36 (s, 1H).

Workup

  1. filtrationfiltered over Celite
  2. additionThe filtrate was acidified to a pH of ˜3 via addition of citric acid
  3. filtrationthe resulting precipitate was collected by vacuum filtration
  4. washwashed with water (2×5 mL)

Sources & evidence

ORD record
ord-adb91c1c11ed46be87783ae9aa37b6ce
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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