4-Chlorobenzylamine → HCID 21192417, compound

HRID 1067261Notes

Reaction equation

HRID 1067261 reaction equation
[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([I:15])=[CH:12][CH:13]=2)[C:8](=[O:16])[C:7]([C:17]([O:19]CC)=O)=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1>>[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([I:15])=[CH:12][CH:13]=2)[C:8](=[O:16])[C:7]([C:17]([NH:28][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([Cl:22])=[CH:24][CH:25]=2)=[O:19])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 21192422HCID 21192422, compound

Product 1

HCID 21192417HCID 21192417, compoundYield 88.7%

Procedure

A slurry of 1.11 g of ethyl 1-(tert-butyl)-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate from Preparation No. 9 in 2.0 g of 4-chlorobenzylamine is heated under argon at 160° C. for 18 hours, then cooled to room temperature and triturated with 1N HCl. The solid is filtered, washed well with water, and dried under vacuum. Flash chromatography using 20% ethyl acetate in dichloromethane provides 1.22 g of the title compound as a white solid.

Workup

  1. customtriturated with 1N HCl
  2. filtrationThe solid is filtered
  3. washwashed well with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2ebdba5005134b75aa26c8fbc7fb6432
Source dataset
uspto-grants-2001_06
Patent number
US06248736B1

Reaction notes

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