Phosphorus oxychloride → HCID 21266474, compound

HRID 566729Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:12][NH:11][C:10](=O)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[C:13]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:12][N:11]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 21266445HCID 21266445, compound

Product 1

HCID 21266474HCID 21266474, compound

Procedure

4-(3-methylphenyl)-5-(4-pyridyl)-1H-pyrid-2-one (33 mg, 0.13 mmole) in POCl3 (2 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 and 283.

Workup

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

Sources & evidence

ORD record: ord-0c3f1672afe44d17b5a064c554050363
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174901B1

Reaction notes

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