Dimethylamine → HCID 23333781, compound

HRID 904149Notes

Reaction equation

HRID 904149 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][NH:10][CH3:11].[CH2:12]=O>O>[ClH:1].[CH3:9][N:10]([CH2:12][C:4]1[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Cl:1])[N:3]=1)[CH3:11]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 811362-Chloro-3-pyridinol

Product 1

HCID 23333781HCID 23333781, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-chloro-3-hydroxypyridine (12.95 g), 50% aqueous dimethylamine (15 ml) and 40% aqueous formaldehyde (10 ml) in water (30 ml) was heated on a steam bath for 21/2 hours and then allowed to stand at room temperature (20°) overnight. The solution was evaporated and the residue was taken up in chloroform. The solution was decanted off from some insoluble material, dried (Na2SO4) and evaporated to small bulk. An excess of ethereal hydrogen chloride was added and the resulting hydrochloride salt was filtered off and crystallised twice from isopropanol to give 2-(dimethylaminomethyl)-5-hydroxy-6-chloropyridine hydrochloride (5.70 g), m.p. 207°-209°.

Workup

  1. customto stand at room temperature
  2. custom(20°) overnight
  3. customThe solution was evaporated
  4. customThe solution was decanted off from some insoluble material
  5. dry with materialdried (Na2SO4)
  6. customevaporated to small bulk
  7. additionAn excess of ethereal hydrogen chloride was added
  8. filtrationthe resulting hydrochloride salt was filtered off
  9. customcrystallised twice from isopropanol

Sources & evidence

ORD record
ord-6bcd67fb6ed143e9aa009038f0d96126
Source dataset
uspto-grants-1980_10
Patent number
US04230714

Reaction notes

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