Acetic Anhydride → HCID 22330154, compound

HRID 586402Notes

Reaction equation

HRID 586402 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:16](OC(=O)C)(=[O:18])[CH3:17].[BH4-].[Na+]>C(O)(=O)C>[C:16]([N:13]1[CH2:14][CH2:15][C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:11][CH2:12]1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 4595574-(3-nitrophenyl)pyridineHCID 4311764Sodium borohydride

Product 1

HCID 22330154HCID 22330154, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 4-(3-nitrophenyl)pyridine (Example 6g) (4.0 g; 20.0 mmol) and acetic anhydride (20 ml) in glacial acetic acid (30 ml) was added sodium borohydride (1.51 g; 40.0 mmol) in portions over one hour. The resulting mixture was stirred at ambient temperature for five days and then poured into ice-water. The mixture was extracted with ethyl acetate, the organic phase was washed with water, dried over magnesium sulphate and concentrated under reduced pressure. The residue was eluted through silica gel with ethyl acetate to yield 6h (1.29 g; 26%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic phase was washed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was eluted through silica gel with ethyl acetate

Sources & evidence

ORD record
ord-312fd64fa6c34bafba15ae3c07f98b32
Source dataset
uspto-grants-2005_08
Patent number
US06936613B2

Reaction notes

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