Acetic Anhydride → HCID 54276587, compound

HRID 728189Notes

Reaction equation

HRID 728189 reaction equation
C(OC(=O)C)(=O)C.[C:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=1)(=[O:10])[CH3:9].[CH2:19]([O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[N+:35]([O-:37])=[O:36])[CH:30]=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)Cl>[C:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]=[CH:30][C:29]2[CH:32]=[CH:33][C:34]([N+:35]([O-:37])=[O:36])=[C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:28]=2)[N:13]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 2204862-ACETAMIDO-6-METHYLPYRIDINEHCID 121117193-(Benzyloxy)-4-nitrobenzaldehyde

Product 1

HCID 54276587HCID 54276587, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of acetic anhydride (6 ml), 2-acetamido-6-methylpyridine (8.00 g) and 3-benzyloxy-4-nitrobenzaldehyde (13.7 g), was heated at 180° C. for 22 hours with stirring. After cooling, the reaction mixture was dissolved in chloroform (150 ml). The solution was washed with aqueous potassium carbonate, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (640 g) by eluting with chloroform and washed with a mixture of ethyl acetate and diisopropyl ether to give 2-acetamido-6-[2-(3-benzyloxy-4-nitrophenyl)vinyl]pyridine (4.80 g).

Workup

  1. temperatureAfter cooling
  2. washThe solution was washed with aqueous potassium carbonate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel (640 g)
  6. washby eluting with chloroform
  7. washwashed with a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-bec2293175374ea4813d313ef5dcdf99
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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