Morpholine → 4-Chloro-5-morpholin-4-yl-2-nitro-N-methyl-aniline

HRID 1258669Notes

Reaction equation

HRID 1258669 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:13][C:14]1[C:21](Cl)=[CH:20][C:17]([NH:18][CH3:19])=[C:16]([N+:23]([O-:25])=[O:24])[CH:15]=1.C(O)(C(F)(F)F)=O.O>CN(C=O)C>[Cl:13][C:14]1[C:21]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:20][C:17]([NH:18][CH3:19])=[C:16]([N+:23]([O-:25])=[O:24])[CH:15]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 2893174,5-Dichloro-n-methyl-2-nitroanilineHCID 22392675Trifluoroacetic acid water

Product 1

HCID 441206484-Chloro-5-morpholin-4-yl-2-nitro-N-methyl-aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Morpholine (174 mg, 2.0 mmol) followed by potassium carbonate (304 mg, 2.2 mmol) were added to a mixture of 4,5-dichloro-N-methyl-2-nitroaniline (442 mg, 2.0 mmol) in DMF (10 mL) and stirred at rt overnight. The reaction mixture was acidified with TFA:H2O 1:1 and purified by chromatography to give the sub-title compound.

Workup

  1. custompurified by chromatography

Sources & evidence

ORD record
ord-dea7111d858740d4a988ebb0ef94247b
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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