Acetic Anhydride → HCID 15515003, compound

HRID 350661Notes

Reaction equation

HRID 350661 reaction equation
[OH:1][C:2]1[C:3]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=2)=[O:11])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:27](OC(=O)C)(=[O:29])[CH3:28]>>[C:27]([O:1][C:2]1[C:3]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=2)=[O:11])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9])(=[O:29])[CH3:28]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 17817653HCID 17817653, compound

Product 1

HCID 15515003HCID 15515003, compoundYield 67%

Procedure

3-Hydroxy-4-methoxy-3′-benzyloxypicolinanilide (20 mg) was dissolved in 1 ml of acetic anhydride, and a reaction was allowed to proceed at 80° C. for 3 hr. The reaction solution was concentrated under the reduced pressure. The concentrate was extracted with chloroform, followed by washing with a saturated sodium hydrogencarbonate solution and then with saturated brine. The washed extract was then dried over anhydrous sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform) to give 15 mg (yield 67%) of title compound.

Workup

  1. concentrationThe reaction solution was concentrated under the reduced pressure
  2. extractionThe concentrate was extracted with chloroform
  3. washby washing with a saturated sodium hydrogencarbonate solution
  4. extractionThe washed extract
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. concentrationwas then concentrated under the reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (chloroform)

Sources & evidence

ORD record
ord-2a339820afd74428b39e66ec350f034f
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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