Acetic Anhydride → HCID 19701593, compound

HRID 862083Notes

Reaction equation

HRID 862083 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][O:20][CH3:21])=[C:6]([CH:17]=1)[C:7]([C:9]1[C:14]([CH:15]=O)=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8].Cl.NO.C([N:27](CC)CC)C.C(OC(=O)C)(=O)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][O:20][CH3:21])=[C:6]([CH:17]=1)[C:7]([C:9]1[C:14]([C:15]#[N:27])=[CH:13][CH:12]=[CH:11][N:10]=1)=[O:8]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 19701633HCID 19701633, compound

Product 1

HCID 19701593HCID 19701593, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-(5-chloro-2-methoxymethoxybenzoyl)-3-formylpyridine (2.34 g), hydroxylamine hydrochloride (532 mg) and triethylamine (775 mg) was added acetonitrile (30 ml), which was stirred for 1.5 hour at room temperature. The reaction mixture was concentrated, which was partitioned with ethyl acetate/water. The organic layer was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate), and concentrated to give 2-(5-chloro-2-methoxymethoxybenzoyl)-3-hydroxylminomethylpyridine (2.39 g). A mixture of this compound and acetic anhydride (15 ml) was heated for one hour under reflux, followed by distilling off acetic anhydride under reduced pressure. The residue was purified by means of 10 a silica gel column chromatography (eluent: ethyl acetate/hexane) to give 2-(5-chloro-2-methoxymethoxybenzoyl)-3-cyanopyridine (1.51 g) (Compound E-12).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwhich was partitioned with ethyl acetate/water
  3. washThe organic layer was washed with a saturated aqueous saline solution
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customto give 2-(5-chloro-2-methoxymethoxybenzoyl)-3-hydroxylminomethylpyridine (2.39 g)
  7. temperaturewas heated for one hour
  8. temperatureunder reflux
  9. distillationby distilling off acetic anhydride under reduced pressure
  10. customThe residue was purified by means of 10 a silica gel column chromatography (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-76c39224c58d4edba7f16aab3aa5a7e2
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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