Sodium hydride → 1-(6-Chloropyridin-3-ylmethyl)-5-[1,3]dioxolan-2-yl-8-methoxy-3,4-dihydro-1H-quinolin-2-one

HRID 503993Notes

Reaction equation

HRID 503993 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][O:5][CH:4]1[C:8]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:20])[NH:13]2.[H][H].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][N:25]=1>CN(C=O)C>[Cl:23][C:24]1[N:25]=[CH:26][C:27]([CH2:30][N:13]2[C:14]3[C:9](=[C:8]([CH:4]4[O:5][CH2:6][CH2:7][O:3]4)[CH:17]=[CH:16][C:15]=3[O:18][CH3:19])[CH2:10][CH2:11][C:12]2=[O:20])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 66596793HCID 66596793, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 866139171-(6-Chloropyridin-3-ylmethyl)-5-[1,3]dioxolan-2-yl-8-methoxy-3,4-dihydro-1H-quinolin-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (55% in oil) (2.1 g) was added in small portions under ice cooling to a DMF solution (70 ml) of 5-(1,3-dioxolan-2-yl)-8-methoxy-3,4-dihydro-1H-quinolin-2-one (10 g), and stirring was carried out at room temperature until the generation of hydrogen stopped. The resulting mixture was cooled with ice again, and a DMF solution (30 ml) of 2-chloro-5-chloromethyl pyridine (9.74 g) was added dropwise. After stirring at room temperature for 4 hours, the reaction mixture was poured into ice water, and the produced insoluble matter was collected by filtration. The solid was washed with water and diethyl ether and dried to thereby obtain 11.84 g (yield: 79%) of 1-(6-chloropyridin-3-ylmethyl)-5-(1,3-dioxolan-2-yl)-8-methoxy-3,4-dihydro-1H-quinolin-2-one as a light yellow solid.

Workup

  1. temperatureThe resulting mixture was cooled with ice again
  2. stirringAfter stirring at room temperature for 4 hours
  3. filtrationthe produced insoluble matter was collected by filtration
  4. washThe solid was washed with water and diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-1fe622ffd87a40738da607d652f8b3f7
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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