Sodium Hydroxide → 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine-N-oxide

HRID 1835426Notes

Reaction equation

HRID 1835426 reaction equation
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([CH3:24])[C:4]=1[C:5]([C:7]1[C:12]([O:13][CH3:14])=[CH:11][N:10]=[CH:9][C:8]=1[Cl:15])=[O:6].ClC1C=CC=C(C(OO)=[O:33])C=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([CH3:24])[C:4]=1[C:5]([C:7]1[C:12]([O:13][CH3:14])=[CH:11][N+:10]([O-:33])=[CH:9][C:8]=1[Cl:15])=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 235035934-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine

Product 1

HCID 235035884-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine-N-oxideYield 951.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A chloroform (60 ml) solution of 3.4 g (1 mmol) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine (compound No. 244) was cooled with ice, 4.1 g (1.6 mmol) of m-chloroperbenzoic acid was added thereto, followed by stirring under cooling with ice for 2 hours, and stirring was further conducted at room temperature for 2 hours. 30 ml of a 0.5 mol/l aqueous sodium hydroxide solution was added to the mixture to terminate the reaction, the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 3.5 g (yield 85%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-methoxypyridine-N-oxide (m.p. 160-166° C.).

Workup

  1. additionwas added
  2. temperatureunder cooling with ice for 2 hours
  3. stirringstirring
  4. customto terminate
  5. customthe reaction
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9ac71803a24e4affbfc1b0bb88671b22
Source dataset
uspto-grants-2004_08
Patent number
US06770662B2

Reaction notes

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