Nitric Acid → 2-Chloro-6-ethoxy-3-nitropyridine

HRID 371171Notes

Reaction equation

HRID 371171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH3:10])[N:3]=1.S(=O)(=O)(O)O.OS(O)(=O)=O.O=S(=O)=O.[N+:25]([O-])([OH:27])=[O:26]>>[Cl:1][C:2]1[C:7]([N+:25]([O-:27])=[O:26])=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH3:10])[N:3]=1

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 24681Fuming sulfuric acidHCID 985632-Chloro-6-ethoxypyridine

Product 1

HCID 202494082-Chloro-6-ethoxy-3-nitropyridineYield 93%

Conditions

Temperature
0 °C

Procedure

157.6 g (1 mole) of 2-chloro-6-ethoxy-pyridine were slowly added over 45 minutes with stirring to a mixture of 190 ml of concentrated sulfuric acid, 190 ml of 24% oleum and 100 ml of 97% nitric acid while keeping the reaction temperature between 20° and 40° C. with cooling and the mixture was allowed to stand for 5 hours while the temperature returned to room temperature. The mixture was cooled to 0° C. and filtered with a glass frit filter. The solid product was suspended in a mixture of 100 g of potassium carbonate and 250 ml of water and the suspension was stirred for 3 hours at 30° C. and was vacuum filtered. The product was washed with water and dried at 40° C. to obtain 192 g (93% yield) of 2-chloro-3-nitro-6-ethoxy-pyridine with a purity of 98%.

Workup

  1. customthe reaction temperature between 20° and 40° C.
  2. temperaturewith cooling
  3. customreturned to room temperature
  4. filtrationfiltered with a glass frit
  5. filtrationfilter
  6. additionThe solid product was suspended in a mixture of 100 g of potassium carbonate and 250 ml of water
  7. filtrationfiltered
  8. washThe product was washed with water
  9. customdried at 40° C.

Sources & evidence

ORD record
ord-6163b3baf9b848d3b0806ad3fb7cec4e
Source dataset
uspto-grants-1985_07
Patent number
US04529800

Reaction notes

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