Piconol → HCID 18357727, compound

HRID 427733Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[C:17]([CH3:18])=[CH:16][C:15]([N+:19]([O-:21])=[O:20])=[CH:14][N:13]=1>CN(C)C=O>[CH3:18][C:17]1[C:12]([O:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:13][CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=1

Participants

Conditions

Temperature: -20 °C

Procedure

2-Pyridylcarbinol (1.96 g, 18 mmol) in dry dimethylformamide (20 ml) was cooled to −20° C. and treated with sodium hydride (0.48 g of 80% dispersion in mineral oil, 16 mmol). The mixture was stirred under argon at −20° C. for one hour then a solution of 2-chloro-3-methyl-5-nitropyridine (2.07 g, 12 mmol) in dry dimethylformamide (10 ml) was added and the mixture was allowed to warn to room temperature over 16 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane (3×100 ml) and 10% aqueous sodium hydroxide solution(75 ml). The combined organics were dried (Na2SO4) and evaporated in vacuo to a residue which was subjected to flash column chromatography with 1:1 ethyl acetate/petroleum ether as eluant to afford the title compound (1.47 g, 51%) as lemon yellow crystals.

Workup

waitto warn to room temperature over 16 hours
customThe solvent was removed in vacuo
customthe residue partitioned between dichloromethane (3×100 ml) and 10% aqueous sodium hydroxide solution(75 ml)
dry with materialThe combined organics were dried (Na2SO4)
customevaporated in vacuo to a residue which

Sources & evidence

ORD record: ord-1bb25614cbb04cd19954d7e973d0c41c
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313145B1

Reaction notes

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