4-Chlorobenzylamine → HCID 178522929, compound

HRID 2086607Notes

Reaction equation

HRID 2086607 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([I:16])[CH:15]=1)[N:12]=[CH:11][C:10]([C:17]([O:19]CC)=O)=[C:9]2[OH:22])(=O)C.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>CCOCC>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:17]([C:10]2[CH:11]=[N:12][C:13]3[C:8]([C:9]=2[OH:22])=[CH:7][C:6]([CH2:5][OH:4])=[CH:15][C:14]=3[I:16])=[O:19])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469656HCID 178469656, compound

Product 1

HCID 178522929HCID 178522929, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of ethyl 6-[(acetyloxy)methyl]-4-hydroxy-8-iodo-3-quinolinecarboxylate (0.90 g) and 4-chlorobenzylamine (2.6 mL) is heated at 180° C. for 1 h. The reaction is cooled to room temperature and diluted with Et2O. The resulting solid is filtered and triturated with acetone to yield 0.74 g (73%) of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-8-iodo-3-quinolinecarboxamide.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. filtrationThe resulting solid is filtered
  3. customtriturated with acetone

Sources & evidence

ORD record
ord-90546b7e020d4564ba0c99e818164ac3
Source dataset
uspto-grants-2004_04
Patent number
US06727248B2

Reaction notes

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