Phosphorus oxychloride → 2-Chloro-4-isopropyl-5,8-dimethylquinoline

HRID 2368689Notes

Reaction equation

HRID 2368689 reaction equation
[CH:1]([C:4]1[C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=[CH:11][C:12]=2[CH3:14])[N:7]=[C:6](O)[CH:5]=1)([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:19]>C1(C)C=CC=CC=1>[Cl:19][C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=[CH:11][C:12]=2[CH3:14])[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178424504HCID 178424504, compound

Product 1

HCID 835270542-Chloro-4-isopropyl-5,8-dimethylquinolineYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-isopropyl-5,8-dimethylquinolin-2-ol (1.30 g, 6.05 mmol), 700 L (1.2 eq) of POCl3 in toluene were reacted as outlined in Scheme 1 above to yield 1.00 g of 2-chloro-4-isopropyl-5,8-dimethylquinoline (71%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.34 (d, J=6.74 Hz, 6 H) 2.71 (s, 3 H) 2.87 (s, 3 H) 4.12 (quin, J=6.74 Hz, 1 H) 7.21 (d, J=7.33 Hz, 1 H) 7.32 (s, 1 H) 7.40 (d, J=7.33 Hz, 1 H).

Sources & evidence

ORD record
ord-f76ff35f47ea42a08d072a4680dad706
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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