Sodium Carbonate → 2-(2-chlorophenyl)-5,7-dihydroxy-8-((2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)chromen-4-one

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Pyridinium chloride	HCID 10176127	—
Reactant	(+)-trans-2-(2-Chloro-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one	HCID 59318486	—
Solvent	Methanol	HCID 887	—
Product	2-(2-chlorophenyl)-5,7-dihydroxy-8-((2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)chromen-4-one	HCID 23643976	—

Reaction Conditions

Temperature	180 °C

Reaction Steps

Molten pyridine hydrochloride (2.5 g, 21 mmol, 10×w/w) was added to compound of example 7 (0.25 g, 0.58 mmol) and heated at 180° C. for 1.5 h. The reaction mixture was cooled to 25° C., diluted with MeOH (10 mL) and basified using Na2CO3 to pH 10. The mixture was filtered and the organic layer was concentrated. The residue was suspended in water (10 mL), stirred for 30 min., filtered and dried to obtain the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07884127B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-aca600141bb04cdaad081c923a9e9550
Source note	uspto-grants-2011_02