3-Hydroxy-2-nitropyridine → HCID 18795892, compound

HRID 1604414Notes

Reaction equation

HRID 1604414 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N+:10]([C:13]1[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][N:14]=1)([O-:12])=[O:11].C(=O)(O)[O-].[Na+]>CO.C(Cl)Cl>[N+:10]([C:13]1[C:18]([O:19][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:17][CH:16]=[CH:15][N:14]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 270573-Hydroxy-2-nitropyridineHCID 76300Ethyl 4-bromobutyrateHCID 516892Sodium Bicarbonate

Product 1

HCID 18795892HCID 18795892, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

This compound was prepared from ethyl 4-bromobutyrate 2 and 2-nitro-3-pyridinol (39) via the procedure of Step (A), supra. Following flash chromatography (silica gel; 1.5% methanol/methylene chloride eluant) a dilute sodium bicarbonate wash of an ether solution of the product was necessary to remove traces of starting phenol. The product (40) was obtained in 76% yield as a pale yelow oil.

Workup

  1. washwash of an ether solution of the product
  2. customto remove traces of starting phenol

Sources & evidence

ORD record
ord-3eecf76c3dc64c77869986bf087c380e
Source dataset
uspto-grants-1999_11
Patent number
US05994362

Reaction notes

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