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

HRID 2737

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-7cc7d41500194b2d804cca39c54e96aa
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731310

Linked notes

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