Acetic Anhydride → HCID 18182484, compound

HRID 1359322Notes

Reaction equation

HRID 1359322 reaction equation
C([O:8][C:9]1[C:10]([CH:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)O)=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)C1C=CC=CC=1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[OH:8][C:9]1[C:10]([CH2:16][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18182406HCID 18182406, compound

Product 1

HCID 18182484HCID 18182484, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.87 g of 3-benzyloxy-2-[(4-methoxyphenyl)hydroxymethyl]-6-methylpyridine, 2.5 ml of acetic acid anhydride and 20 ml of pyridine was heated under stirring for 4 hours in an oil bath kept at 120° C. After the reaction solution was evaporated, water was added thereto. The mixture was extracted with ethyl acetate, and the organic phase was washed with brine, dried over anhydrous magnesium sulfate and concentrated. To the residue were added 20 ml of methanol, 10 ml of tetrahydrofuran and a catalytic amount of 10% palladium/carbon, followed by stirring for 10 hours in a hydrogen atmosphere. After the catalyst was filtered off, the filtrate was concentrated. Then, the crystals were washed with diethyl ether, to give 320 mg of the target compound.

Workup

  1. temperaturewas heated
  2. customkept at 120° C
  3. customAfter the reaction solution was evaporated
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic phase was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. additionTo the residue were added 20 ml of methanol, 10 ml of tetrahydrofuran
  10. stirringby stirring for 10 hours in a hydrogen atmosphere
  11. filtrationAfter the catalyst was filtered off
  12. concentrationthe filtrate was concentrated
  13. washThen, the crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-fe98fd26e5e84e4a957a8e4671a961bd
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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