Acetic Anhydride → HCID 11345023, compound

HRID 1818897Notes

Reaction equation

HRID 1818897 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:13])[CH:5]=[C:6]2[CH2:11][CH2:10][O:9][C:8](=[O:12])[C:7]=12.C(N(CC)CC)C.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(#N)C>[O:12]=[C:8]1[C:7]2=[C:2]([NH:1][C:21](=[O:23])[CH3:22])[N:3]=[C:4]([CH3:13])[CH:5]=[C:6]2[CH2:11][CH2:10][O:9]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11458007HCID 11458007, compound

Product 1

HCID 11345023HCID 11345023, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-amino-6-methyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on (200 g, 1.122 mmol) was dissolved in 6 mL of anhydrous acetonitrile, and then dropwisely added with triethylamine (0.63 mL, 4.490 mmol) and actic anhydride (0.42 mL, 4.490 mmol) in this order and then heated to reflux for about 20 hours under the nitrogen atmosphere. The mixture was concentrated under reduced pressure, added with 15 mL of a saturated solution of sodium carbonate and 15 mL of distilled water and then extracted twice with 40 mL of methylene chloride. The resulting organic layer was dried with anhydrous sodium sulfate, and filtered. A silica gel column chromatography (5% MeOH/MC) was performed on the resulting residue and 219 mg (89%) of N-(1-oxo-6-methyl-3,4-dihydro-pyrano[3,4-c]pyridine-8-yl)-acetamide was obtained in white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for about 20 hours under the nitrogen atmosphere
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionadded with 15 mL of a saturated solution of sodium carbonate and 15 mL of distilled water
  5. extractionextracted twice with 40 mL of methylene chloride
  6. dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-203d9621b6da40f78f40dbef1058d3c1
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

Loading…