Morpholine → 4-(4-Nitrobenzyl)morpholine

HRID 1841515Notes

Reaction equation

HRID 1841515 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 7831834-(4-Nitrobenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Nitrobenzylbromide (E.0) is treated with morpholine and potassium carbonate in acetone to give 4-(4-nitrobenzyl)morpholine (E.1) of Chart E. The nitro group is reduced with platinum on carbon and hydrogen gas to afford the aniline E.2. Iodination employing ICI or NIS provides the amine E.3 which is then treated with diethyl ethoxymethylenemalonate to give the enamine E.4. Cyclization with phosphorous pentoxide in methanesulfonic acid affords the quinoline ester E.5. Aminolysis with p-chlorobenzylamine at elevated temperatures gives the amide E.6. Coupling with an acetylene employing PdCl2(PPh3)2 and copper iodide and subsequent cyclization provides the desired pyrroloquinolones E.7.

Sources & evidence

ORD record
ord-44bb64f3ebef4d7db0b7b43b2b24463a
Source dataset
uspto-grants-2004_01
Patent number
US06683181B2

Reaction notes

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