Sodium Carbonate → HCID 178524549, compound

HRID 1896449Notes

Reaction equation

HRID 1896449 reaction equation
[C:1]([O-:4])([O-])=[O:2].[Na+].[Na+].C[C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][CH:15]=[N:16][C:9]=12.[O-][Mn](=O)(=O)=O.[K+]>O>[N:16]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][C:8]=2[C:1]([OH:4])=[O:2])[NH:14][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 516875Potassium Permanganate2×HCID 178428360HCID 178428360, compound

Product 1

HCID 178524549HCID 178524549, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Na2CO3 (3.3 g, 1 eq, 31.5 mmol) and water (200 ml) are added to product 7-methyl-3H-imidazo[4,5-b]pyridine x176 (4.2 g, 31.5 mmol). The reaction mixture is heated until boiled, which caused its transformation into a solution. KMnO4 (12.5 g, 2.5 eq, 78.9 mmol) is added in small portions to the obtained boiling solution. After KMnO4 is added completely, the reaction mixture is additionally kept at 100° C. for 1 h and cooled to 50-60° C. MnO2 is filtered off, and the residue is additionally washed with hot water (2×50 ml) on a filter. The obtained aqueous solution is evaporated in vacuum to a volume of 50 ml, cooled to 5° C., and acidified with 10% HCl to pH 2-3. The obtained suspension is kept at 5° C. for 1 h. The formed precipitate is separated by filtration, washed with ice-cold water (2×10 ml), and vacuum-dried (1 mm Hg) over P2O5 overnight to give 2.06 g of 3H-imidazo[4,5-b]pyridine-7-carboxylic acid x177.

Workup

  1. temperatureThe reaction mixture is heated
  2. filtrationMnO2 is filtered off
  3. washthe residue is additionally washed with hot water (2×50 ml) on a filter
  4. customThe obtained aqueous solution is evaporated in vacuum to a volume of 50 ml
  5. temperaturecooled to 5° C.
  6. waitThe obtained suspension is kept at 5° C. for 1 h
  7. customThe formed precipitate is separated by filtration
  8. washwashed with ice-cold water (2×10 ml)
  9. dry with materialvacuum-dried (1 mm Hg) over P2O5 overnight

Sources & evidence

ORD record
ord-3a8141de9f2f485988694222e7ceee32
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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