7-Aminoquinoline → 9-Oxo-9H-fluorene-2-carboxylic acid quinolin-7-yl amide

HRID 494258Notes

Reaction equation

HRID 494258 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[O:12]=[C:13]1[C:25]2[CH:24]=[C:23]([C:26](O)=[O:27])[CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:26]([C:23]3[CH:22]=[CH:21][C:20]4[C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:13](=[O:12])[C:25]=4[CH:24]=3)=[O:27])[CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 113777-AminoquinolineHCID 69913Fluorenone-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 576826739-Oxo-9H-fluorene-2-carboxylic acid quinolin-7-yl amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-aminoquinoline (D55) (35 mg, 0.24 mmol) in DCM (3 ml) was added 9-oxo-9H-fluorene-2-carboxylic acid (60 mg, 0.27 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (68 mg, 0.36 mmol) and 4-dimethylaminopyridine (5 mg, 0.04 mmol) and the reaction stirred at room temperature then at reflux until complete by tlc. After cooling to room temperature the resultant precipitate was filtered off to give the title compound as an off-white solid. MS(ES): MH+ 351, M-H+ 349

Workup

  1. temperatureat reflux until complete by tlc
  2. filtrationwas filtered off

Sources & evidence

ORD record
ord-e46a805cfcff40e3a1a945274cb69073
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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