Ammonium Chloride → HCID 18667518, compound

HRID 1059873Notes

Reaction equation

HRID 1059873 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1.C([Li])CCC.CN(C)[C:18](=[O:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][C:18](=[O:20])[CH3:19])[CH:4]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 585150HCID 585150, compoundHCID 178418339Butyllithium

Product 1

HCID 18667518HCID 18667518, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-dimethylamino-2-methylpyridine (1.30 g) in tetrahydrofuran (13 ml) was added a solution of n-butyllithium in n-hexane (1.56M, 7.34 ml) dropwise at −50° C. under a nitrogen atmosphere, and the mixture was warmed to 0° C. The mixture was cooled to −50° C., and N,N-dimethylacetamide (1.15 ml) was added dropwise. Then the mixture was warmed to room temperature, poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate (100 ml×3). The combined organic layer was washed with brine, dried over sodium sulfate and-evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 50 g, 20% methanol in dichloromethane) to give 1-(4-dimethylaminopyridin-2-yl)propan-2-one (1.29 g).

Workup

  1. temperatureThe mixture was cooled to −50° C.
  2. temperatureThen the mixture was warmed to room temperature
  3. extractionextracted with ethyl acetate (100 ml×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. custom-evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel 50 g, 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f6b774101ea24d96b6de3d59f1ae96e5
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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