2-Chloropyridine → 2-(N-Methyl-N-(2-pyridyl)amino)ethanol

HRID 968310Notes

Reaction equation

HRID 968310 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][NH:9][CH2:10][CH2:11][OH:12]>O>[CH3:8][N:9]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[CH2:10][CH2:11][OH:12]

Participants

4

Reactant 2

HCID 79772-ChloropyridineHCID 80162-(Methylamino)ethanol

Product 1

HCID 7374202-(N-Methyl-N-(2-pyridyl)amino)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-chloropyridine (12 g) and 2-(methylamino)ethanol (100 ml) are stirred under nitrogen at 120° C. for 18 hours. Cool to room temperature and then pour into iced water (250 ml). Extract with ethyl acetate (2×200 ml). Dry over sodium sulfate. Filter. Evaporate to dryness. The crude product is distilled in vacuo to give 10.3 g of N-methyl-N-(2-pyridinyl)-2-aminoethanol, boiling at 110° C./1.0 mmHg.

Workup

  1. extractionExtract with ethyl acetate (2×200 ml)
  2. dry with materialDry over sodium sulfate
  3. filtrationFilter
  4. customEvaporate to dryness
  5. distillationThe crude product is distilled in vacuo

Sources & evidence

ORD record
ord-4bf01dbf793944bea83251652a15f1e9
Source dataset
uspto-grants-2005_10
Patent number
US06958355B2

Reaction notes

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