Iodine chloride → 7-Chloro-3-(2-chlorophenyl)-4-iodo-2,6-naphthyridine 2-oxide

HRID 1502378Notes

Reaction equation

HRID 1502378 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[CH:9][N:10]=1)[CH:5]=[N:6][OH:7].[I:20]Cl>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8]([C:11]([I:20])=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[N+:6]([O-:7])=[CH:5]2)=[CH:9][N:10]=1

Participants

5

Reactant 2

HCID 24640Iodine chlorideHCID 1364131892-Chloro-5-((2-chlorophenyl)ethynyl)isonicotinaldehyde oxime

Product 1

HCID 866749537-Chloro-3-(2-chlorophenyl)-4-iodo-2,6-naphthyridine 2-oxide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a slurry of 2-chloro-5-((2-chlorophenyl)ethynyl)isonicotinaldehyde oxime (850 mg, 2.9 mmol) in acetonitrile (8 mL) was added iodine monochloride (1.4 g, 8.8 mmol). The reaction mixture instantly became homogeneous and was stirred at room temperature. After 15 minutes the reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford an orange residue that was used in the next step without further purification (1.2 g, 98%).

Workup

  1. washwashed with water (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford an orange residue that
  7. customwas used in the next step without further purification (1.2 g, 98%)

Sources & evidence

ORD record
ord-1eee33be305c4130b3ec1ce960a9b22d
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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