8-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1) → HCID 45140184, compound

HRID 574285Notes

Reaction equation

HRID 574285 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2.[N:15]1([CH2:21][CH2:22][N:23]([CH2:35][CH2:36][CH3:37])[CH:24]2[CH2:33][CH2:32][C:31]3[C:30]([OH:34])=[CH:29][CH:28]=[CH:27][C:26]=3[CH2:25]2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>>[OH:34][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:31]=1[CH2:32][CH2:33][CH:24]([N:23]([CH2:35][CH2:36][CH3:37])[CH2:22][CH2:21][N:15]1[CH2:20][CH2:19][N:18]([CH2:3][C:4]3[CH:13]=[CH:12][C:11]([OH:14])=[C:10]4[C:5]=3[CH:6]=[CH:7][CH:8]=[N:9]4)[CH2:17][CH2:16]1)[CH2:25]2

Participants

3

Reactant 2

HCID 122695968-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)HCID 60167428HCID 60167428, compound

Product 1

HCID 45140184HCID 45140184, compoundYield 77.5%

Procedure

This compound was prepared following the procedure H in which compound 11 (0.18 g, 0.8 mmol) and 9b (0.23 g, 0.72 mmol) were used to afford 12b as yellow solid (0.265 g, 59%). 1H NMR of salt (400 MHz, DMSO-d6) δ ppm 0.84-0.87 (t, 3H, J=6 Hz), 1.79-1.81 (bs, 4H), 2.298 (bs, 1H), 2.476-2.48 (m, 2H), 2.74 (s, 2H), 2.96-3.02 (t, 1H, J=12 Hz), 3.122 (bs, 3H), 3.34-3.65 (m, 12H), 6.50-6.52 (d, 1H, J=8 Hz), 6.55-6.57 (d, 1H, J=8 Hz), 6.93-6.96 (t, 1H, J=6 Hz), 7.06-7.08 (d, 1H, J=8 Hz), 7.32-7.34 (d, 1H, J=8 Hz), 7.44-7.46 (m, 1H), 8.66-8.68 (d, 1H, J=8 Hz), 8.77-8.78 (d, 1H, J=4 Hz). The hydrochloride salt mp 252-255° C. Analysis calculated for (C29H43N4O4.5, 4HCl) C, H, N.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-6ff0affbe34c4b5aa0121582097c00bd
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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