Acetic Anhydride → 2-(2-Acetoxy-1,1-dimethylethylamino)-3-nitro-5-(trifluoromethyl)pyridine

HRID 1370108Notes

Reaction equation

HRID 1370108 reaction equation
[CH3:1][C:2]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[CH:9][N:8]=1)([CH3:5])[CH2:3][OH:4].[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([O:4][CH2:3][C:2]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([C:16]([F:18])([F:19])[F:17])=[CH:9][N:8]=1)([CH3:1])[CH3:5])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 700154552-(1,1-Dimethyl-2-hydroxyethylamino)-3-nitro-5-(trifluoromethyl)pyridine

Product 1

HCID 185097712-(2-Acetoxy-1,1-dimethylethylamino)-3-nitro-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(1,1-dimethyl-2-hydroxyethylamino)-3-nitro-5-(trifluoromethyl)pyridine (1.2 g) in pyridine (12 mL) was added acetic anhydride (0.811 mL), and the mixture was stirred at room temperature under nitrogen atmosphere for 4 hours. The resulting mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The separated organic layer was washed successively with 1 N-hydrochloric acid, water, an aqueous saturated sodium hydrogencarbonate solution and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo to give 2-(2-acetoxy-1,1-dimethylethylamino)-3-nitro-5-(trifluoromethyl)pyridine (1.39 g) as a yellow oil.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe separated organic layer was washed successively with 1 N-hydrochloric acid, water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0bd74885f7734b26ba57c33d52f06a32
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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