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

HRID 2093541Notes

Reaction equation

HRID 2093541 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-072f473d63a74900bfdf720f4e09a6bc
Source dataset
uspto-grants-2013_05
Patent number
US08445504B2

Reaction notes

Loading…