Formic Acid → HCID 20392480, compound

HRID 1863245Notes

Reaction equation

HRID 1863245 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9]Cl)[C:5](CCl)=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[CH:20]([OH:22])=O.[OH-:23].[Na+]>O>[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][OH:23])[C:5]([CH2:20][OH:22])=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 20392483HCID 20392483, compound

Product 1

HCID 20392480HCID 20392480, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 20 g of crude 2-methyl-4,5-di-(chloromethyl)-6-benzyl-pyridin-3-ol in 40 g of 75% strength formic acid is heated under reflux. After 10 minutes, a solution of 10.7 g of sodium hydroxide in 15 ml of water is added and heating is continued for 1 hour. The mixture is concentrated to dryness under reduced pressure. The residue is digested in 100 ml of acetone, the insoluble constituent is filtered off, the filtrate is concentrated and the residue thus obtained is boiled for 1/2 hour in 50 ml of water. After again concentrating the mixture, the residue is recrystallized from acetone. 5.7 g of 2-methyl-4,5-di-(hydroxymethyl)-6-benzyl-pyridin-3-ol, of melting point 158°-159° C., are obtained.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. waitis continued for 1 hour
  4. concentrationThe mixture is concentrated to dryness under reduced pressure
  5. filtrationthe insoluble constituent is filtered off
  6. concentrationthe filtrate is concentrated
  7. customthe residue thus obtained
  8. concentrationAfter again concentrating the mixture
  9. customthe residue is recrystallized from acetone

Sources & evidence

ORD record
ord-20145db998964cb1a1d972df89ab20d0
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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