p-Fluoronitrobenzene → 4-(4-Nitrophenyl)-morpholin-3-ON

HRID 1817780Notes

Reaction equation

NC1C=CC(N2CCOCC2=O)=CC=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][C:16]1=[O:21].[H-].[Na+].F[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1>>[N+:31]([C:28]1[CH:29]=[CH:30][C:25]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C:16]2=[O:21])=[CH:26][CH:27]=1)([O-:33])=[O:32]

Participants

Reactant 4

HCID 9590p-Fluoronitrobenzene

HCID 24758Sodium hydride

HCID 669533-Morpholinone

HCID 111948544-(4-Aminophenyl)morpholin-3-one

Product 1

HCID 114473754-(4-Nitrophenyl)-morpholin-3-ON

Procedure

In contrast, WO-A 01/47919 also describes a preparation method for 4-(4-aminophenyl)-3-morpholinone (I). In this method, morpholin-3-one (V) is first deprotonated with sodium hydride and then reacted with 4-fluoronitrobenzene (VI) to give 4-(4-nitrophenyl)-3-morpholinone (VII). Catalytic hydrogenation of (VII) with hydrogen over palladium on activated carbon in tetrahydrofuran as a solvent affords 4-(4-aminophenyl)-3-morpholinone (I):

Sources & evidence

ORD record: ord-937ea0c265bc4e1b956b6bf9dad55be8
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598378B2

Reaction notes

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