4-(2-Nitro-4-(pyridin-3-yl)phenyl)morpholine → 2-Morpholino-5-(pyridin-3-yl)aniline

HRID 1431250Notes

Reaction equation

HRID 1431250 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][C:5]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)([O-])=O>CO.[Pd]>[O:19]1[CH2:20][CH2:21][N:16]([C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:9][C:4]=2[NH2:1])[CH2:17][CH2:18]1

Participants

4

Reactant 1

HCID 596312104-(2-Nitro-4-(pyridin-3-yl)phenyl)morpholine

Product 1

HCID 596310952-Morpholino-5-(pyridin-3-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(2-nitro-4-(pyridin-3-yl)phenyl)morpholine (300 mg, 0.24 mmol) in MeOH (140 mL) was reduced using a continuous flow hydrogenation reactor (flow rate: 1 mL/min, 10% mol Pd/C, temperature 40° C., H2 pressure: 10 bar) to give 2-morpholino-5-(pyridin-3-yl)aniline.

Sources & evidence

ORD record
ord-e4945ef787b94253afe64ba564528e56
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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