Ammonium Chloride → (5-Chloro-4-methoxy-6-methylpyridin-3-yl)methanol

HRID 81691Notes

Reaction equation

HRID 81691 reaction equation
[Cl:1][C:2]1[C:3]([CH3:14])=[N:4][CH:5]=[C:6]([C:11]=1[O:12][CH3:13])[C:7](OC)=[O:8].[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[CH3:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 58201192HCID 58201192, compound

Product 1

HCID 58201212(5-Chloro-4-methoxy-6-methylpyridin-3-yl)methanolYield 105.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above methyl 5-chloro-4-methoxy-6-methylnicotinate (1.0 g) was dissolved in 30 ml of methanol, and sodium borohydride (1.75 g) was then added to the solution. The resulting mixture was heated under reflux for 1 hour. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution under cooling on ice, followed by extraction with chloroform three times. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled away, so as to obtain the title compound (0.92 g) as an oily substance.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureunder cooling on ice
  4. extractionfollowed by extraction with chloroform three times
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was then distilled away

Sources & evidence

ORD record
ord-507fd6d30a2547578f0352b50e67a46d
Source dataset
uspto-grants-2014_09
Patent number
US08846703B2

Reaction notes

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