Acetic Anhydride → HCID 18458647, compound

HRID 2304808Notes

Reaction equation

HRID 2304808 reaction equation
[OH:1][CH:2]1[C:7]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][C:9]=2[O:18][CH3:19])=[CH:6][CH2:5][N:4]([CH3:20])[CH2:3]1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[C:21]([O:1][CH:2]1[C:7]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[CH:10][C:9]=2[O:18][CH3:19])=[CH:6][CH2:5][N:4]([CH3:20])[CH2:3]1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 99256571,2,3,6-Tetrahydro-1-methyl-4-(2,4,6-trimethoxyphenyl)-3-pyridinol

Product 1

HCID 18458647HCID 18458647, compound

Conditions

Temperature
100 °C

Procedure

2.79 g (10 mmol) of 3(R,S)-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydropyridine (VII) were dissolved in 15 ml of acetic anhydride and stirred at 100° C. for 4 h. The solution was then evaporated in vacuo in a rotary evaporator and the residue was dissolved in 10 ml of water, adjusted to pH>12 with sodium hydroxide solution and extracted twice with 20 ml of ethyl acetate each time. The combined organic phases were washed with 10 ml of saturated sodium chloride solution, then dried over sodium sulfate and evaporated in vacuo on a rotary evaporator.

Workup

  1. customThe solution was then evaporated in vacuo in a rotary evaporator
  2. dissolutionthe residue was dissolved in 10 ml of water
  3. extractionextracted twice with 20 ml of ethyl acetate each time
  4. washThe combined organic phases were washed with 10 ml of saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo on a rotary evaporator

Sources & evidence

ORD record
ord-b585caff145748e29dc194389e82d348
Source dataset
uspto-grants-2002_08
Patent number
US06437136B1

Reaction notes

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