Acetic Anhydride → HCID 86647438, compound

HRID 2071166Notes

Reaction equation

HRID 2071166 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([N:10]([CH3:12])[CH3:11])[N:3]=1.[CH3:13][C:14](OC(C)=O)=[O:15]>N1C=CC=CC=1>[C:14]([O:9][CH2:8][C:6]1[CH:5]=[C:4]([N:10]([CH3:12])[CH3:11])[N:3]=[C:2]([Cl:1])[CH:7]=1)(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86647439HCID 86647439, compound

Product 1

HCID 86647438HCID 86647438, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of (2-chloro-6-(dimethylamino)pyridin-4-yl)methanol in 7 mL of pyridine was added 1.2 mL of Ac2O. After the solution was stirred for 12 h, the solution was concentrated, and saturated NaHCO3 solution was added to pH=7. The aqueous layer was extracted with EtOAc, and the organic layer was washed with H2O (15 mL) and brine (15 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (15% EtOAc/hexanes) provided (2-chloro-6-(dimethylamino)pyridin-4-yl)methyl acetate as a yellow oil with some impurity.

Workup

  1. concentrationthe solution was concentrated
  2. additionsaturated NaHCO3 solution was added to pH=7
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe organic layer was washed with H2O (15 mL) and brine (15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash silica gel chromatography (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-80d465a60e404f20bf5e0c52be47aba3
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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