4-Chlorobenzylamine → HCID 178522895, compound

HRID 1168525Notes

Reaction equation

HRID 1168525 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][C:16]([C:20]([O:22]CC)=O)=[C:15]2[OH:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>>[CH2:1]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:26][N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][C:16]([C:20]([NH:39][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([Cl:33])=[CH:35][CH:36]=1)=[O:22])=[C:15]2[OH:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469619HCID 178469619, compound

Product 1

HCID 178522895HCID 178522895, compound

Conditions

Temperature
200 °C

Procedure

A mixture of ethyl 8-((benzylamino)methyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxylate (Preparation 28, 513 mg) and 4-chlorobenzylamine (2.5 mL) is heated at 200° C. for 20 min. The mixture is concentrated, and the remaining oil is taken up in chloroform and applied to a silica gel column. The column is eluted with 1% methanol/chloroform followed by 2-4% methanol/chloroform to afford 483 mg of the title compound after crystallization from ethyl acetate/ether. Physical characteristics: M.p. 214-216° C.; 1H NMR (CDCl3) δ2.46, 3.59, 3.71, 3.86, 4.28, 4.67, 7.28-7.43, 7.53, 8.25, 8.84, 10.5. Anal. Found: C, 67.68; H, 5.89; N, 10.52; Cl, 6.64.

Workup

  1. concentrationThe mixture is concentrated
  2. washThe column is eluted with 1% methanol/chloroform

Sources & evidence

ORD record
ord-24c2a94ca26c4c698c22afff25dc0fb9
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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