Acetic Anhydride → (4-Nitropyridin-2-yl)methyl acetate

HRID 600262Notes

Reaction equation

HRID 600262 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].CC1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][N:10]1O>C(O)C>[N+:15]([C:13]1[CH:12]=[CH:11][N:10]=[C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH:14]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 689075252-Methyl-4-nitro-pyridin-1-ol

Product 1

HCID 14761430(4-Nitropyridin-2-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To acetic anhydride (60 mL, 0.635 mol) at 110° C. under a nitrogen atmosphere was added 2-methyl-4-nitro-pyridin-1-ol (15)(17.1 g, 111 mmol) portionwise over 1 minute. After approximately 2 minutes the solution began to darken and heating maintained at 100-120° C. for 30 minutes and then allowed to cool to 80° C. Ethanol (60 mL) was added and the solution was concentrated under vacuum; residue slurried in water (140 mL) and the mixture neutralised with NaHCO3 (ca. 40 g). The aqueous liquor was extracted with ethyl acetate (4×100 mL, combined extracts washed with brine (2×100 mL, dried over Na2SO4, concentrated in vacuo to a crude oil. The material was subjected to flash chromatography eluent hexane:TBME (2:1). A brown oil was isolated, single peak in LC-MS analysis, (6.44 g 30%); m/z (LC-MS, ESP), RT=3.65 mins, (M+H) 197.

Workup

  1. temperatureheating
  2. temperatureto cool to 80° C
  3. concentrationthe solution was concentrated under vacuum
  4. extractionThe aqueous liquor was extracted with ethyl acetate (4×100 mL
  5. washcombined extracts washed with brine (2×100 mL
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo to a crude oil
  8. customA brown oil was isolated

Sources & evidence

ORD record
ord-d85576e209be4dd79a73c92375c005cd
Source dataset
uspto-grants-2011_03
Patent number
US07902193B2

Reaction notes

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