Cesium carbonate → 2-Nitro-5-(3-oxo-morpholin-4-yl)-benzonitrile

HRID 1819529Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][C:14]1=[O:19].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[N+:10]([C:5]1[CH:4]=[CH:3][C:2]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C:14]2=[O:19])=[CH:9][C:6]=1[C:7]#[N:8])([O-:12])=[O:11]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 5-chloro-2-nitrobenzonitrile (2.41 g), morpholin-3-one (2 g), cesium carbonate (6.45 g), tris(dibenzylideneacetone)dipalladium (120 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (230 mg) in 30 ml dioxane was heated for 24 h at 120° C. The reaction mixture was cooled to 25° C., diluted with CH2Cl2 and filtered through decalite. The organic layer was washed with water and brine and purified by chromatography (silica gel, AcOEt) to yield 2-nitro-5-(3-oxo-morpholin-4-yl)-benzonitrile as a yellow solid (1.77 g). MH+=248.3

Workup

temperatureThe reaction mixture was cooled to 25° C.
filtrationfiltered through decalite
washThe organic layer was washed with water and brine
custompurified by chromatography (silica gel, AcOEt)

Sources & evidence

ORD record: ord-3b1a6f10f0c04c6d9afe283b5c7b5af1
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601752B2

Reaction notes

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