Sodium Hydroxide → 4-[[(6-chloropyridin-3-yl)methyl](methyl)amino]furan-2(5H)-one

HRID 451338

Reaction equation

[CH3:1][NH:2][C:3]1[CH2:7][O:6][C:5](=[O:8])[CH:4]=1.[OH-].[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][N:13]=1>C(COC)OC>[Cl:11][C:12]1[N:13]=[CH:14][C:15]([CH2:18][N:2]([CH3:1])[C:3]2[CH2:7][O:6][C:5](=[O:8])[CH:4]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

30 g of 4-(methylamino)furan-2(5H)-one (Example 11) are initially charged in 450 ml of dimethoxyethane at room temperature. Subsequently, 12.6 g of sodium hydroxide are added and, at 40° C., 225 g of a 20% solution of 2-chloro-5-(chloromethyl)pyridine in dimethoxyethane are metered in. The mixture is stirred at 50° C. for a further 6 h. The solvent is substantially removed under reduced pressure and the residue is admixed with 300 ml of water. The solids are filtered off, washed with 150 ml of water and dried under reduced pressure. 58.7 g of 4-([[6-chloropyridin-3-yl]methyl](methy)amino)furan-2(5H)-one are obtained with a purity of 94% (this corresponds to 87% yield).

Workup

customThe solvent is substantially removed under reduced pressure
filtrationThe solids are filtered off
washwashed with 150 ml of water
customdried under reduced pressure

Sources & evidence

ORD record: ord-8236c195a16443edb1720bb9f06d759e
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487112B2

Linked notes

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