Sodium hydride → t-Butyl N-[5-(pyridine-2-yloxy)-2-nitrophenyl]-N-methylcarbamate

HRID 2303851Notes

Reaction equation

HRID 2303851 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:9]1[CH:10]=[CH:11][C:12]([N+:24]([O-:26])=[O:25])=[C:13]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=1.[H-].[Na+]>CN(C)C=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][C:9]1[CH:10]=[CH:11][C:12]([N+:24]([O-:26])=[O:25])=[C:13]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamateHCID 178516071HCID 178516071, compound

Product 1

HCID 18461366t-Butyl N-[5-(pyridine-2-yloxy)-2-nitrophenyl]-N-methylcarbamateYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By using 0.76 g of 2-hydroxypyridine, 2.29 g of t-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate, 0.35 g of sodium hydride (55% by weight) and 10 ml of anhydrous N,N-dimethylformamide, reaction and purification were carried out in a similar manner to that described in Reference Example 6, whereby 0.36 g of the title compound were obtained.

Sources & evidence

ORD record
ord-861c47b5c33c4b5c98a7beaf6405c37f
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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