Morpholino(3-nitrophenyl)methanone → 3-(Morpholine-4-carbonyl)aniline

HRID 1939298Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8])([O-])=O>C(O)C.O.NN.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[C:7]([N:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

The compound ([13]-(132)-158) (8.63 g) prepared in Example 83 was dissolved in ethanol (400 ml), and the solution was heated to 50° C. To the suspention, a solution of 10% Pd/C (2.25 g) in ethanol and hydrazine monohydrate (4.4 ml) were added to the solution. The mixture was stirred for 30 minutes. After the reaction was completed, the catalyst was removed by filtration through celite. The solution was concentrated, and the residue was purified by silica gel column chromatography (Kieselgel 60=120 g, ethyl acetate) to obtain the above-captioned compound ([13]-(133)-158) (7.57 g) as a white solid.

Workup

customthe catalyst was removed by filtration through celite
concentrationThe solution was concentrated
customthe residue was purified by silica gel column chromatography (Kieselgel 60=120 g, ethyl acetate)

Sources & evidence

ORD record: ord-fd76663c68e2443892be863fbf696e61
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696118

Reaction notes

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