Acetic Anhydride → (2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)methyl acetate

HRID 1913434Notes

Reaction equation

HRID 1913434 reaction equation
[CH3:1][C:2]1[N+:7]([O-])=[C:6]2[O:9][CH2:10][CH2:11][O:12][C:5]2=[CH:4][CH:3]=1.[CH3:13][C:14]([O:16]C(C)=O)=[O:15]>>[C:14]([O:16][CH2:1][C:2]1[N:7]=[C:6]2[O:9][CH2:10][CH2:11][O:12][C:5]2=[CH:4][CH:3]=1)(=[O:15])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 21873713HCID 21873713, compound

Product 1

HCID 67407401(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)methyl acetateYield 99%

Procedure

A solution of 6-methyl-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine 5-oxide (60 g, 0.36 mol) in Ac2O (500 mL) was stirred at reflux for 5 hours. The reaction was cooled and the solvent was removed in vacuo to yield (2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-6-yl)methyl acetate (75 g, 99%) as a dark oil, which was used in the next step without further purification.

Workup

  1. temperatureat reflux for 5 hours
  2. temperatureThe reaction was cooled
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dae8cda7dcbf4173a2cd09e4e33d5357
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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