Water → 2-Chloro-4-isopropoxy-5-nitropyridine

HRID 518826Notes

Reaction equation

HRID 518826 reaction equation
[CH3:1][CH:2]([CH3:4])[O-:3].[Na+].[Cl:6][C:7]1[CH:12]=[C:11](Cl)[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=1.O>CN(C=O)C>[Cl:6][C:7]1[CH:12]=[C:11]([O:3][CH:2]([CH3:4])[CH3:1])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 109204432-Propanol, sodium salt (1:1)2×HCID 122757652,4-Dichloro-5-nitropyridine

Product 1

HCID 866979922-Chloro-4-isopropoxy-5-nitropyridineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.38 g of sodium isopropoxide are added to a solution of 2.6 g of 2.4-dichloro-5-nitropyridine in 39 ml of DMF. The reaction medium is stirred at ambient temperature for 1 h 15 and 3.18 g of sodium isopropoxide are added. The reaction medium is stirred for a further 15 minutes and then the mixture is poured into 200 ml of water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification is carried out by flash chromatography on silica gel (40-63 microns), elution being carried out with a heptane/ethyl acetate mixture (90/10 to 80/20). 1.78 g of 2-chloro-5-nitro-4-(propan-2-yloxy)pyridine are obtained in the form of a pale yellow solid.

Workup

  1. additionare added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. washis carried out by flash chromatography on silica gel (40-63 microns), elution

Sources & evidence

ORD record
ord-6ce76442920749218b7376c694ac50e3
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

Loading…