Pyridine → HCID 73178437, compound

HRID 1357037Notes

Reaction equation

HRID 1357037 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:10][O:11][N:12]=[C:13]([C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[N:16]=1)[CH3:14].N1C=CC=CC=1.[C:29](Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:29]([O:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:10][O:11][N:12]=[C:13]([C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[N:16]=1)[CH3:14])(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 85448910HCID 85448910, compound

Product 1

HCID 73178437HCID 73178437, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.2 g (0.67 mmol) of 1-(4,6-dimethyl-2-pyridinyl)ethanone O-[(2-hydroxy-3-methoxyphenyl)methyl]oxime was dissolved in 5 ml of methylene chloride. The resultant solution was added with 0.11 g (1.34 mmol) of pyridine, 5 mg of 4-(N,N-dimethylamino)pyridine and 0.12 g (1.00 mmol) of pivalic chloride. The obtained mixture was heated to reach the reflux temperature and stirred for 5 hours to complete a reaction. The reacted solution was washed with water and saturated saline solution in sequence, and the resultant nonaqueous layer was dried with anhydrous magnesium sulfate. The mixture was then condensed under reduced pressure to obtain a crude product. The crude product was then purified by means of silica gel column chromatography (eluate; hexane:ethyl acetate=9:1 (v/v)) to obtain the target compound in an amount of 0.2 g.

Workup

  1. temperatureThe obtained mixture was heated
  2. customa reaction
  3. washThe reacted solution was washed with water and saturated saline solution in sequence
  4. dry with materialthe resultant nonaqueous layer was dried with anhydrous magnesium sulfate
  5. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-5aa61d50c3af453581821efa11072a10
Source dataset
uspto-grants-2003_07
Patent number
US06589967B1

Reaction notes

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