4-Chlorobenzylamine → HCID 178522948, compound

HRID 1168196Notes

Reaction equation

HRID 1168196 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=2)[N:5]=[N:4][C:3]=1[C:19]([O:21]CC)=O.[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>CCOCC>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:19]([C:3]2[N:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[CH:8][CH:7]=3)=[O:21])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178470442HCID 178470442, compound

Product 1

HCID 178522948HCID 178522948, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of ethyl 4-hydroxy-6-(4-morpholinylmethyl)-3-cinnolinecarboxylate (Preparation 11, 0.382 g) and 4-chlorobenzylamine (1.46 mL) is heated to 80° C. for 30 min over which time a solid forms. The reaction is diluted with Et2O and the resulting solid is collected and dried to yield 0.443 g (89%) of the desired compound as an off-white solid. Physical characteristics are as follows: m.p. 277-280° C. (dec); 1H NMR (DMSO-d6) δ10.12, 8.09, 7.86, 7.74, 7.40, 4.56, 3.63, 3.58, 2.38; MS (ESI+) for C21H21ClN4O3 m/z 413.0 (M+H)+MS (ESI−), 410.9 (M−H)−.

Workup

  1. customthe resulting solid is collected
  2. customdried

Sources & evidence

ORD record
ord-136afe688a1542f7a58ec67a5e8d3405
Source dataset
uspto-grants-2003_09
Patent number
US06624160B2

Reaction notes

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