Acetic Anhydride → HCID 178474345, compound

HRID 537024Notes

Reaction equation

HRID 537024 reaction equation
COC1C=C(OC)C=C[C:4]=1[CH2:5][NH:6][C:7]1[N+:8]([O-:17])=[CH:9][C:10]([CH3:16])=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1.C(OC(=O)C)(=[O:26])C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:16][C:10]1[C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]([NH:6][C:5](=[O:26])[CH3:4])=[N+:8]([O-:17])[CH:9]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178490961HCID 178490961, compound

Product 1

HCID 178474345HCID 178474345, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(2,4-dimethoxybenzyl)-5-methyl-4-nitropyridin-2-amine 1-oxide (1.1 g, 3.5 mmol) in DCM (20 mL) and TFA (3 mL) was allowed to stir at rt for 4 h. The reaction mixture was concentrated and the residue was dissolved in DCM (20 mL). To this solution were added TEA (2.5 mL, 17.7 mmol) and acetic anhydride (0.4 g, 4.3 mmol). The reaction mixture was allowed to stir at rt overnight and then filtered to give N-(5-methyl-4-nitro-1-oxidopyridin-2-yl)acetamide (0.73 g, 98%) which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in DCM (20 mL)
  3. stirringto stir at rt overnight
  4. filtrationfiltered

Sources & evidence

ORD record
ord-fe68412fa4544edd807c53fc572c95bb
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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