Acetic Anhydride → 7-Methyl-2H-pyrano[2,3-b]pyridin-2-one

HRID 657162Notes

Reaction equation

HRID 657162 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH:9]=O)=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:18][C:19](OC(C)=O)=[O:20]>>[CH3:1][C:2]1[N:7]=[C:6]2[O:8][C:19](=[O:20])[CH:18]=[CH:9][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 127224622-Hydroxy-6-methylpyridine-3-carbaldehyde

Product 1

HCID 688173287-Methyl-2H-pyrano[2,3-b]pyridin-2-oneYield 30%

Conditions

Temperature
120 °C

Procedure

To 6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbaldehyde (318 mg, 2.3 mmol) in Ac2O (3 mL) was added Et3N (1 mL). The reaction was heated at 120° C. for 18 hours. The reaction was concentrated and the resulting material was dissolved in MeOH and loaded onto silica gel and evaporated. Purification by column chromatography (silica gel) using a hexanes/ethyl acetate gradient (0-100% EtOAc) provided the desired product as a solid (80 mg, 30%). LCMS (ES+) m/z 162 (MH+).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe resulting material was dissolved in MeOH
  3. customevaporated
  4. customPurification by column chromatography (silica gel)

Sources & evidence

ORD record
ord-f4110bd669924f3ea8be82a5f2aa9c8f
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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