Sodium hydride → 5-Chloro-1-(4-methoxy-benzyl)-3-nitro-1H-pyridin-2-one

HRID 1478243Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[H-].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=[O:8])[N:6]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 5-chloro-3-nitropyridin-2-ol (12 g, 68.8 mmol) in DMF (80 ml) was added in several portions NaH (3.30 g, 83 mmol) at 0° C. The reaction mixture was stirred in the ice-bath for 2 hours. Then 4-methoxybenzyl chloride (11.19 ml, 83 mmol) was added and the reaction mixture was heated at 80° C. for 1 hour. The reaction mixture was quenched with aqueous saturated NaHCO3 solution and extracted twice with EtOAc. The organic layers were washed with brine, combined, dried over sodium sulphate, filtered and evaporated. The crude material was taken up in n-heptane/AcOEt 10:1 and the suspension was kept in the sonic bath for 10 minutes. After filtration the filtrate was washed with n-heptane and dried in vacuum to obtain 11.84 g (40.2 mmol, 58.4% yield) of the title compound as a greenish solid. LCMS: (M+H)=295; tR=0.94 min (LC-MS 4). 1H-NMR (d6-DMSO, 400 MHz) 8.72 (d, 1H) 8.56 (d, 1H) 7.36 (d, 2H) 6.94 (d, 2H) 5.13 (s, 2H) 3.74 (s, 3H).

Workup

customThe reaction mixture was quenched with aqueous saturated NaHCO3 solution
extractionextracted twice with EtOAc
washThe organic layers were washed with brine
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated
filtrationAfter filtration the filtrate
washwas washed with n-heptane
customdried in vacuum

Sources & evidence

ORD record: ord-5abc34129d91467492daad6f06dec904
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403827B2

Reaction notes

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