Phosphorus oxychloride → HCID 21266511, compound

HRID 566723Notes

Reaction equation

HRID 566723 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:8]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:9][C:10](=O)[NH:11][CH:12]=2)[CH:2]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:10]1[CH:9]=[C:8]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[C:7]([C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([CH3:20])[CH:2]=2)=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21266437HCID 21266437, compound

Product 1

HCID 21266511HCID 21266511, compound

Procedure

5-m-tolyl-1H-[4,4′]bipyridinyl-2-one (262 mg, 1.0 mmole) in POCl3 (5 mL) was heated to 105° C. for 12 hr. POCl3 was removed under reduced pressure. The residue was diluted with methylene chloride and was carefully quenched with aqueous sodium carbonate. Standard work up, followed by purification (silica gel, hexane/ethyl acetate) gave the title compound. MS (m/z): Calcd. C17H13N2Cl (M+): 280.5, found (M+H)+: 281.0 and 283.1.

Workup

  1. customPOCl3 was removed under reduced pressure
  2. additionThe residue was diluted with methylene chloride
  3. customwas carefully quenched with aqueous sodium carbonate
  4. customfollowed by purification (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2cb25b9e3aa248a5a440ab189f0a1f92
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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