Phosphorus oxychloride → 2-Chloro-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one

HRID 1986969Notes

Reaction equation

[CH3:1][C:2]1([CH3:14])[CH2:11][C:10]2[NH:9][C:8](=O)[CH:7]=[CH:6][C:5]=2[C:4](=[O:13])[CH2:3]1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:8]1[CH:7]=[CH:6][C:5]2[C:4](=[O:13])[CH2:3][C:2]([CH3:14])([CH3:1])[CH2:11][C:10]=2[N:9]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 135163797,7-dimethyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

Product 1

HCID 148125452-Chloro-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-oneYield 60%

Procedure

In analogy to (Shanazarov, A. K.; Kuzovkin, V. A.; Chistjakov, V. V.; Granik, V. G. Khim. Geterotsikl. Soedin. 1991, (1) 86-92.) 7,7-dimethyl-7,8-dihydro-1H,6H-quinoline-2,5-dione was treated with phosphoryl chloride (POCl3) to give the title compound as a gray solid in 60% yield.

Sources & evidence

ORD record: ord-12a0870e821748d092d04e8053782be7
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550482B2

Reaction notes

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