Water → HCID 86717657, compound

HRID 2200850Notes

Reaction equation

HRID 2200850 reaction equation
[CH3:1][C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([OH:13])=[O:12])=[O:3].[OH2:14].C[N:16]([CH:18]=O)[CH3:17]>>[C:5]([O:4][CH2:2][O:12][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:4][C:2](=[O:3])[CH3:1])(=[O:14])[C:10]1[CH:9]=[CH:8][CH:17]=[N:16][CH:18]=1

Participants

4

Reactant 3

HCID 962WaterHCID 2244Aspirin2×HCID 6228Dimethylformamide

Product 1

HCID 86717657HCID 86717657, compoundYield 50%

Conditions

Temperature
45 °C

Procedure

TEA (0.08 ml, 0.68 mmol, 1.2 eq) and methyl formyl reagent [259] (0.1 g, 0.56 mmol, 1.0 eq) was added to a solution of aspirin [4154] and 2-acetoxybenzoic acid, (0.1 g, 0.56 mmol, 1.0 eq) in DMF (2 ml). The reaction mixture was heated at 45° C. for 16 h, followed by cooling to room temperature and dilution with water. The organic material was extracted with ethyl acetate, was washed with water dried over Na2SO4 and evaporated under vacuum to get crude product. The crude product was purified by silica gel column chromatography (ethyl acetate in cyclohexane 100-200 mesh) to yield a dark colored sticky product [318], ((2-acetoxybenzoyl)oxy)methyl nicotinate, (0.09 g, 50%).

Workup

  1. temperatureby cooling to room temperature
  2. extractionThe organic material was extracted with ethyl acetate
  3. washwas washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum
  6. customto get crude product
  7. customThe crude product was purified by silica gel column chromatography (ethyl acetate in cyclohexane 100-200 mesh)

Sources & evidence

ORD record
ord-f3e09f22a3bd4224b0111e66e5bf25c2
Source dataset
uspto-grants-2016_06
Patent number
US09359376B2

Reaction notes

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