Phosphorus oxychloride → 2-Chloro-4-isopropyl-1,8-naphthyridine

HRID 1892259Notes

Reaction equation

HRID 1892259 reaction equation
[CH:1]([C:4]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=O)[CH:5]=1)([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:17]>C1(C)C=CC=CC=1>[Cl:17][C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67083031HCID 67083031, compound

Product 1

HCID 866692872-Chloro-4-isopropyl-1,8-naphthyridineYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-isopropyl-1,8-naphthyridin-2(1H)-one (800 mg, 4.3 mmol) and 475 L of POCl3 in toluene were reacted as outlined in Scheme 1 to give the desired 2-chloro-4-isopropyl-1,8-naphthyridine (690 mg, 79%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.41 (d, J=6.74 Hz, 6 H) 3.68 (dq, J=7.03, 6.84 Hz, 1 H) 7.38 (s, 1 H) 7.52 (dd, J=8.35, 4.25 Hz, 1 H) 8.44 (dd, J=8.50, 2.05 Hz, 1 H) 9.09 (dd, 1 H).

Sources & evidence

ORD record
ord-37df7b799ca94639857c3dcab290394e
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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