4-Chlorobenzylamine → HCID 178522858, compound

HRID 1068027Notes

Reaction equation

HRID 1068027 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:19](OCC)=[O:20].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>C(Cl)Cl>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:19]([C:3]2[CH:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:8][CH:7]=3)=[O:20])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469521HCID 178469521, compound

Product 1

HCID 178522858HCID 178522858, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A solution of ethyl 4-hydroxy-6-(tetrahydro-2H-pyran-4-ylmethyl)-3-quinolinecarboxylate (0.315 g) from Preparation No. 51 and 4-chlorobenzylamine (0.61 nL) is heated to 180° C. for 1 h. The reaction mixture is cooled to 65° C. and diluted with CH2Cl2. Hexanes are added to initiate precipitation of the product. The resulting solid is collected and dried to yield 0.33 g of N-(4-chlorobenzyl)-4-hydroxy-6-(tetrahydro-2H-pyran-4-ylmethyl)-3-quinolinecarboxamide as an off-white solid.

Workup

  1. customprecipitation of the product
  2. customThe resulting solid is collected
  3. customdried

Sources & evidence

ORD record
ord-8fff3fa153414afb85c0946f1519044f
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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