[CH2:1]([N:3](CC)[CH2:4]C)C.[Cl:8][C:9]1[CH:18]=[C:17]([Cl:19])[C:16]([OH:20])=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([CH:21]=O)=[N:14]2.Cl.CNC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[ClH:8].[Cl:8][C:9]1[CH:18]=[C:17]([Cl:19])[C:16]([OH:20])=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([CH2:21][N:3]([CH3:4])[CH3:1])=[N:14]2
Triethylamine (0.55 mL) was added dropwise to a stirred solution of 5,7-dichloro-8-hydroxyquinoline-2-carboxaldehyde 17 (1.0 g, 4.13 mmol) and dimethylamine hydrochloride (365 mg, 4.48 mmol) in 1,2-dichloroethane (50 mL). After 5 minutes, sodium triacetoxyborohydride (1.2 g, 5.66 mmol) was added portionwise over 5 minutes. The mixture was then allowed to stir at RT overnight. Dichloromethane (100 mL) was added, the mixture washed with saturated sodium bicarbonate (50 mL×3), dried (Na2SO4), and concentrated. The resulting residue was extracted with diethyl ether (50 mL×4), the ethereal extracts combined and concentrated. Concentrated hydrochloric acid (5 mL) was then added and the mixture concentrated in vacuo. The process was repeated twice. The residue, after washing with dichloromethane, gave 5,7-dichloro-2-dimethylaminomethyl-quinolin-8-ol hydrochloride (PBT 1033) as a pale straw-coloured solid (0.96 g, 73%). 1H NMR (DMSO-d6, 400 MHz): δ 10.80 (s, 1 H), 10.40 (br, 1 H), 8.60 (d, J=8.6, 1 H), 7.92 (s, 1 H), 7.78 (d, J=8.6, 1 H), 4.83 (d, J=5.3, 2 H), 2.94 (s, 3 H), 2.92 (s, 3 H).
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