Acetic Anhydride → N-(6-chloro-3-nitropyridin-2-yl)acetamide

HRID 1823507

Reaction equation

HRID 1823507 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>O1CCCC1>[Cl:13][C:6]1[N:5]=[C:4]([NH:3][C:14](=[O:16])[CH3:15])[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 2783822N-(6-chloro-3-nitropyridin-2-yl)acetamideYield 8.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (120 mg, 5 mmole) in tetrahydrofuran(10 ml), a solution of 2-amino-3-nitro-6-chloropyridine (870 mg, 5 mmole) in 20 ml of tetrahydrofuran (20 ml) was added. The reaction mixture was stirred at room temperature for 30 min. A solution of acetic anhydride (377 μl, 6 mmole) in tetrahydrofuran (10 ml) was added and stirred at room temperature overnight. The reaction mixture was quenched with water and concentrated under reduced pressure. The crude product was dissolved in dichloromethane and washed with brine. The organic layer was dried with sodium sulfate and then concentrated under vacuo. The crude was purified by flash chromatography, eluting 78% hexane:22% ethyl acetate to give a yellow product (88 mg).

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction mixture was quenched with water
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe crude product was dissolved in dichloromethane
  5. washwashed with brine
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated under vacuo
  8. customThe crude was purified by flash chromatography
  9. washeluting 78% hexane

Sources & evidence

ORD record
ord-570f5d7a808e433bb52f75a4fda83ea1
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Linked notes

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