Dimethylamine → HCID 86647439, compound

HRID 2071165Notes

Reaction equation

HRID 2071165 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4](Cl)[N:3]=1.C(OCC)(=O)C.O.[NH:18]([CH3:20])[CH3:19]>>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([N:18]([CH3:20])[CH3:19])[N:3]=1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 8857Ethyl AcetateHCID 2794840(2,6-Dichloropyridin-4-yl)methanol

Product 1

HCID 86647439HCID 86647439, compound

Procedure

A mixture of crude (2,6-dichloropyridin-4-yl)methanol in 7 mL of (CH3)2NH (40 wt % solution in H2O) was stirred at r.t. for 45 min. The temperature was increased to 50° C., and the solution was stirred at 50° C. for about 24 h. Ethyl acetate and H2O (15 mL) were added, and the aqueous layer was extracted with EtOAc. The combined extracts were washed with brine, and the aqueous layer was extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (40% EtOAc/hexanes) provided 1.01 g of (2-chloro-6-(dimethylamino)pyridin-4-yl)methanol with some impurity (unreacted starting material).

Workup

  1. temperatureThe temperature was increased to 50° C.
  2. stirringthe solution was stirred at 50° C. for about 24 h
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash silica gel chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8f2286edbd2c4ac6b3e12b4ef8bd506d
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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