Cesium carbonate → Methyl 4-(morpholin-3-on-4-yl)-3-nitro-benzoate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3-Morpholinone	HCID 66953	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Methyl 4-bromo-3-nitrobenzoate	HCID 2736829	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	Methyl 4-(morpholin-3-on-4-yl)-3-nitro-benzoate	HCID 67049467	—

Reaction Conditions

Temperature	95 °C

Reaction Steps

1.00 g (3.85 mmol) methyl 4-bromo-3-nitro-benzoate are dissolved in 6 ml dioxane with 389 mg (3.85 mmol) morpholin-3-one under a nitrogen atmosphere and 36.6 mg (40 μmol) tris-(dibenzylideneacetone)-dipalladium (0), 67.1 mg (116 μmol) xantphos and 1.75 g (5.38 mmol) caesium carbonate are added. Under a nitrogen atmosphere and with stirring, the reaction mixture is heated to 95° C. for 16 hours. Then it is filtered, the solution is evaporated down i. vac. and evaporated with ether. The residue is further reacted without any more purification. Yield: 1.31 g (quantitative)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08791103B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-20c332e220f248b5b45b77cef2d5ba4c
Source note	uspto-grants-2014_07