Acetic Anhydride → HCID 57950386, compound

HRID 1020695Notes

Reaction equation

HRID 1020695 reaction equation
[N:1]1[C:2]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][N+:15]([O-])=[CH:14][CH:13]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(OC(=O)C)(=[O:21])C>>[N:1]1[C:2]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:21])[CH:13]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 68657324HCID 68657324, compound

Product 1

HCID 57950386HCID 57950386, compoundYield 63%

Conditions

Temperature
80 °C

Procedure

4-(Imidazo[1,2-a]pyridin-2-ylmethoxy)pyridine 1-oxide (1.50 g, 6.25 mmol) was heated at 140° C. in acetic anhydride (18 mL) for 2 h. The mixture was concentrated and heated at 80° C. for 2 h in 1:1 MeOH/H2O (50 mL). The resulting black solution was concentrated. The material was then partially dissolved in iPrOH (20 mL). Et2O (70 mL) was added, and the mixture was allowed to sit at ambient temperature for 1 h. The resulting solids were collected by filtration and washed with Et2O to yield the title compound (951 mg, 63%) as a dark brown solid: 1H NMR (300 MHz, DMSO-d6) δ 11.08 (br s, 1H), 8.54 (m, 1H), 8.01 (s, 1H), 7.53 (d, J=9.0 Hz, 1H), 7.26-7.23 (m, 2H), 6.90 (m, 1H), 5.89-5.87 (m, 2H), 5.14 (s, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. concentrationThe resulting black solution was concentrated
  3. dissolutionThe material was then partially dissolved in iPrOH (20 mL)
  4. additionEt2O (70 mL) was added
  5. filtrationThe resulting solids were collected by filtration
  6. washwashed with Et2O

Sources & evidence

ORD record
ord-addfeb507bc34f0b93455c50fda5e190
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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