7-Chloro-8-hydroxyquinoline

[Ru(dmphen)2Cl2] (100mg, 0.17mmol) and 7-chloro-HQ (30.5mg, 0.17mmol) were added to 8mL of ethanol-water mixture (1:1) in a 15mL pressure tube. The mixture was heated at 60C for 5h while protected from light. The purple solution was allowed to cool to room temperature and poured into 50mL of dH2O. Addition of a saturated aq. KPF6 solution (ca. 1mL) produced a purple precipitate that was collected by vacuum filtration. The purification of the solid was carried out by flash chromatography (silica gel, loaded in MeCN). A gradient was run, and the pure complex eluted at 0.2% KNO3, 8-10% H2O in MeCN. The product fractions were concentrated under reduced pressure, and a saturated aq. solution of KPF6 was added, followed by extraction of the complex into CH2Cl2. The solvent was removed under reduced pressure to give a purple solid. Yield: 64mg (45%). 1H NMR (CD3CN): delta 8.43-8.48 (m, 2H), 8.30-8.32 (m, 1H), 7.98-8.19 (m, 5H), 7.67 (dd, J=8.3, 2.5Hz, 1H), 7.61 (d, J=8.9Hz, 1H), 7.34-7.39 (m, 2H), 6.96-7.25 (m, 2H), 6.63-6.68 (m, 1H), 6.48-6.59 (m, 1H), 2.69-2.70 (m, 3H), 2.16 (s, 3H), 1.93 (s, 3H), 1.82 (s, 3H); purity by HPLC=96%; ESI MS calcd for C74H56Cl2N10O2Ru2 [M]2+ 695.11, found 695.1 [M]2+; UV/Vis (CH3CN): lambdamax (epsilon×10-3) 495nm (12).General procedure: The synthesis of metal complexes was performed following a previously described procedure [1a]. [Ru(dmphen)2Cl2] (100mg, 0.17mmol) and HQ (0.19mmol) were added to 4mL of ethylene glycol in a 15mL pressure tube. The mixture was heated at 100-120C for 2h while protected from light. The purple solution was allowed to cool to room temperature and poured into 50mL of dH2O. Addition of a saturated aq. KPF6 solution (ca. 1mL) produced a purple precipitate that was collected by vacuum filtration. The purification of the solid was carried out by flash chromatography (silica gel, loaded in MeCN). A gradient was run, and the pure complex eluted at 0.2% KNO3, 5-10% H2O in MeCN. The product fractions were concentrated under reduced pressure, and a saturated aq. solution of KPF6 was added, followed by extraction of the complex into CH2Cl2. The solvent was removed under reduced pressure to give the product as a solid.

7-chloroquinolin-8-ol is an intermediate used in the preparation of qunoline derivative for the treatment of neuropathy.

Molecular Weight:179.60
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:179.0137915
Monoisotopic Mass:179.0137915
Topological Polar Surface Area:33.1
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes